Sissy Social Work free porn video

Sissy Social Work I couldn't help myself. Wearing tight, sheer panties all day at work, or thongs with a string up my ass. Or pantyhose against my ass and cock, feeling them rub against me every move I made, leaking constantly. Or even garters with a belt if I was feeling particularly daring. I shaved nearly every day, everything below the waist. Practice makes perfect and I was able to get to everything, even around my ass, with strategically placed mirrors. I even managed to avoid masturbating while shaving after the first few times, although I always had a hard cock while scraping away stubble. Yes, I was obsessed and distracted. My work definitely suffered and it showed. I work in a sales organization, non-client facing, and the sales reps weren't exactly thrilled with the late deliverables and blamed me for losing contracts. So it's not surprising that I was called into a meeting with my boss's boss (my boss being on the road almost all the time). Kev was basically operations manager, reporting to the CEO/owner who lived in some tax haven, so essentially Kev was top dog. In the brutal world of sales, Kev stood out by being a genuinely nice guy. Always had something nice to say to everyone, didn't stand on hierarchy, and crucially (for the business) always kept his head under extreme pressure. A drink of cool water on a parching day. Kev was mid-50s, about 6'2", slim but powerful. He did some sort of martial arts, I've seen him in his white robes and black belt, and worked out a lot. I didn't know much else about him but he made sure people did their job, no one was bullied or mistreated, and didn't take sides - other than the side of keeping the business going smoothly. So I wasn't particularly nervous but damn well knew that I'd get some sort of gentle probing as to why my work had fallen off, what was bothering me, etc. I had a story worked out about girlfriend trouble and planned to apologize and get out of the meeting as quickly as possible. I'm Ray, by the way. I'm 29 and single, living in a small apartment in a decent part of town (having had moved from a great apartment in a terrible neighborhood). I'm a runner so slim and, as you've learned, discovering a lot of things about my sexuality now that I stayed clean shaven and pantied. I'd had a few flings with women but nothing that lasted. So to be addicted to sissy porn, pantyhose porn, and crossdressing sex porn was probably not doing much for either my career or my romantic opportunities. I knocked and pushed the door which was already partly open. Kev had a massive office with a couple of couches and a relatively small, clean desk. It was almost like a living room with comfy chairs and the couches arranged around a low table. Kev was wearing a tight compression-like shirt and tight pants that came down to his knees, almost like bike riding ones. His package wasn't outlined exactly but definitely was sticking out proud. My eyes went wide as I walked in. "Hi Ray, thanks for coming up. Sorry about my attire, just back from a ride and haven't had the time for a quick shower and change yet. You don't mind, do you? I'm not too sweaty, it's just these riding clothes." He smiled and indicated that I should sit on a couch with him next to me. "No Kev, that's fine, I was just surprised that's all." I moved to sit down and felt my pantyhose pulling at my crotch. I tried to surreptitiously rearrange myself to sit comfortably. "So Ray, we're known each other for nearly three years. I took you on as a newbie and we trained you, seeing your innate talent, and you've been a Godsend to the team. Always on time, willing to go the extra mile, do the overtime, whatever it takes to enable our team to win. Sales is about teamwork..." Kev droned on and I started to tune out, having heard all this before, and hoping that my semi-hard-on didn't show through my tight suit trousers. Here it comes, I thought. "Thing is, Ray, for the past couple of months or so we've all noticed a precipitous falling off of your work. You're here on time but you're distracted, you seem to be elsewhere a lot of the time. Even just now I could see that you weren't really listening to me even though you're right next to me. What's going on?" I squirmed around some more. This was even worse than what I expected. "I...well, I've had some girlfriend trouble recently Kev. I'm really sorry, I'll get back to how I was before, you don't need to worry about me..." I continued with a few bland platitudes but definitely wasn't fooling Kev. "You're totally distracted Ray. You used to have a laser-like focus on the team and their needs. It's almost like, well, you're no longer fulfilled in some way, so your concentration is on yourself rather than us and the business." Then my world collapsed. "Is it these hose you're wearing, Ray?" Kev put his hand on my thigh and rubbed back and forth. "Are they distracting you? I couldn't wear these cycling shorts all the time either, they're so form-fitting I can't really keep my mind on my job while wearing them. They're fine for cycling but that's it. Do you need to wear pantyhose to work every day, and whatever else you wear under those very tight trousers?" My mouth fell open and I just stared in horror at Kev. WTF?!? How did he know? "No, I...I, no, I'm not...I'm..." I stuttered. "Stand up Ray." I stood up, intending to walk out. I could get another job. Probably. Maybe. "Undo your belt, Ray." I tried to look away from Kev who was now standing next to me but couldn't. He remained calm and, well, encouraging, not demanding at all, and had a slight smile on his face. His handsome face, framed by longish streaked blonde hair, with full lips, and... "Are you still distracted, Ray? Do you need help?" Kev asked with a smile. I don't know why I didn't just turn and walk out. Maybe I could sue for harassment or something. But I didn't...and undid my belt, unbuttoned the waist, pulled down the zipper and let my pants drop down to my ankles. I felt both embarrassed and excited, almost dizzy with it all, my sheer hose clearly showing my hard cock pushing out, standing straight up against my stomach. Kev looked and pulled my shirt up to have an unobstructed view. "Ray, no wonder you don't get anything done here lately! Basically you're edging yourself all day long. You must be soaking wet by the time you leave. Just look at the state of you now, and it's just after 11:00 in the morning! I understand now, but let's think about how to resolve this." Kev put his hands on my shoulders and turned me so my back was to him. "You do keep yourself in good shape, Ray. You should be able to attract women easily. Unless that's not what you're looking for..." Kev pulled himself into me and I felt his large package rubbing against my ass. "Is this what you need, Ray? A man to rub up against you? Tell me..." Kev was holding my hips and rubbing himself against me. I could feel his hardness against my crack, rubbing up and down. "Ooooh, mmmm, I...oh, Kev, this, ah, I..." I mumbled incoherently. Kev pushed one of his fingers into my mouth, and put his lips against my ear. "Suck on this, Ray, don't talk. I know exactly what you need..." I sucked on his finger as he kept rubbing against me a minute or so that seemed like a lifetime. Was this really what I needed? My God, I felt that I could cum just from his touch on my ass, without touching me elsewhere. But then his hands wandered down to my crotch and traced my cock and balls with his fingers, a light touch but ever so erotic, just teasing me with his fingertips. He turned me back to face him. I leaned forward for a kiss but Kev just smiled. "We need to get you to focus, Ray. Now concentrate..." Kev slowly but firmly pushed me down to my knees, facing his crotch. Kev was hard now, his cock outlined in his tight clinging pants. I stared at his impressive form and reached out to touch it. "That's it, Ray, feel. If this what you need? Feel all over, feel my ass. Is this what you want?" I touched everywhere, rubbing, prodding, caressing. I couldn't believe it, here in the boss's office, fondling his cock, balls and ass through the tight Lyra, me in pantyhose on my knees in front of him. I couldn't help myself, I licked his cock through the material while fondling his firm ass. Ohhh...what next? "Clearly you need some release to concentrate on your work, young Ray. Lay down on the floor on your back. Don't worry, it's thick carpet, and you're not the first one to find yourself on your back in my office. Maybe the first man in pantyhose to do so, however..." Kev knelt in front of me, pulled my legs wide apart, and lay on top, still in his shorts, his package pushing into my cock. He held my thighs and started an up and down motion. I was panting as he rubbed against me. He reached up and pinched my nipples, hard, and I couldn't help myself but I grabbed his lovely ass and pushed him into me as hard as I could and rocked my hips against him. We were in sync, pounding against each other, and I couldn't last another minute - I squealed and let go as I pushed hard, squirting into my wet hose, over and over as Kev kept on pushing and rubbing against me. Kev felt my spasms and it spurred him on, bucking against me as if he was actually fucking me, over and over until he grunted and held me hard against him as he kept rubbing while his cock pulsed out jets of cum inside his shorts. We held each other as we kept flooding our clothes until finally both of us were spent. Kev gave me a gentle kiss and pushed himself to his knees. "Feel better now, Ray? I'm happy to help keep you focused on a regular basis. If your work doesn't improve, and I mean immediately, you won't be working here so hopefully this little incentive will help. Won't it, Ray?" "Thank you Kev, I promise to focus. But...can I see you again, maybe outside of work?" "I'll send you my home address on IM. Be there at 8 tonight, Ray. Now get cleaned up in the bathroom and get back to work." I quickly left, wearing my pants, and peeled off my soaking wet pantyhose in the bathroom. I cleaned myself as much as I could with toilet paper and as I was alone I quickly washed the hose in the sink and stuffed them into a bag. I was now commando but wasn't concerned, I was totally sated sexually. For the first time in I don't know how many months, I actually had a very productive afternoon, got most of the backlog out of the way and even managed to reach out to various team members to ask about their needs. One woman said, "What, is the old Ray back again? Thank goodness!" It felt great to be in control, happy and enthusiastic. Was that all it took, a quick fuck (of sorts)? I think it was more about sharing my secret with someone else, someone who seemed to understand, and admitting to myself (finally!) that I was attracted to men, or at least to Kev. I stayed until about 6:30 to get on top of all the various tasks I've let slide, and went back to my apartment for a quick shower. I decided to wear my best - garter belt and stockings, some high heels and a little black dress that I got recently. I had a bra with small breast forms, all courtesy of the internet, and of course until now no one else had seen me dressed. I had a red wig as well and took my time to get it right, and used just a bit of makeup - eyes, blusher and of course lips. I reckoned I could use some lash work and the mascara definitely helped. I blew myself a kiss in the mirror - not bad if I did say so myself. I could probably just about pass in dim lighting. I had a very quick sandwich and minced out to my car. Had to lose the heels to drive (how do women put up with this every day?) but finally got to Kev's place - a large house set back from the street with its own drive. Not vulgar but certainly substantial. I parked next to a massive Range Rover and navigated the stones on the drive to the door. I raised my hand to ring the bell and realized that I had neglected my nails - oh well, next time! Kev answered quickly - was he waiting for me nearby? "Oh my, what do we have here! I was expecting Ray but you're even better. What do I call you, my lovely?" "Raylynn. Pleased to meet you, Kev." Kev kissed the back of my hand. He was wearing what I could only guess were yoga pants - skin-tight, light green that were a second skin, with nothing underneath so that everything from the waist down was very clearly outlined. Wow...he really must work out daily. He had on another compression shirt that showed off his strong chest and abs. "Please, Raylynn, come on in. Had I known you were dressing up I would have worn something more formal." "You're perfect...I mean, you look perfect, uh, wonderful, Kev." I blushed - too much going on and with me wearing my full girly outfit I was tongue-tied. Kev just smiled and led me into his massive kitchen where he had a range of delicious hors d'oeuvres laid out. Kev popped open a bottle of vintage champagne and poured me a glass. "To us, Raylynn." It was magnificent and we made inconsequential conversation while we nibbled. We took our drinks and the bottle with us to the living room, another massive space with a huge TV in the corner and sofas and chairs scattered throughout. "Come sit with me, gorgeous." We sat together and Kev took my glass out of my hand and placed it on the table next to his. He took my head in his hands and leaned in for a kiss. Soft, gentle, he teased me with his tongue and I whimpered a little. I felt so submissive when I was dressed, I couldn't help it. Kev wasn't aggressive or even assertive, but I couldn't help yielding to him. He pulled back and looked me in the eyes. "Raylynn, no wonder you've been flustered at work. Here, with me, you can be yourself. I'll help you find who you really are." I felt butterflies in my stomach - what did he mean? "Here, feel this - do you like it?" He took my hand and placed it on his large mound between his legs. I rubbed it then used my fingers to trace his long cock and down to his balls. "Yes Raylynn, it's my cock. Do you like it?" "Y..yes, I do." I rubbed it some more and pulled on his cock until it was straight and hard, then rubbed it again. "I know. So do I. It's nice to have you rub me. Have you been with a man before, Raylynn?" "No, never. Well, earlier today..." I giggled a little. "Not before that?" "No, Kev, never. But I fantasize about it all the time. I watch videos and look at photos, read stories, and..." "I know dear girl. You're obsessed. But here I am!" Kev reached under my dress and cupped my cock and balls in his hand. He pulled my dress up to my waist, spread my legs and kept rubbing through my silken panties. "I want to take you close tonight, Raylynn. I want you so crazy with desire that you beg me for release. Wet and hot, dripping and hard, for what will seem forever. Is that what you want?" "I want to please you, Kev." "Ah, good answer my little one. You are and you will." Kev pulled me up onto his lap facing him. I could feel his erection underneath me as he kept rubbing me through my panties. He reached down and quickly pulled his pants down, then positioned his cock in the crack of my ass as he started rubbing me again. "Oh you feel so nice, your ass is wonderful against my cock." He pushed me back onto him and back again, back and forth, pushing against me. Suddenly he spread his legs and he put me down on the carpet in front of him as he sat on the sofa. "Lick, Raylynn. You want to, don't you? Go ahead." My first cock - I took a tentative lick then put the head in my mouth. It was velvety and smooth, the cut mushroom head filling my mouth. I tongued it, kept my teeth away and did my best to please Kev. After a few minutes he pulled me back up to him and we kissed. "Nice, isn't it? Let's make ourselves more comfortable." Onto the bedroom - another huge room with a great big bed in the middle. An old fashioned iron headboard appeared to offer ample opportunities for clamps and ropes - was Kev into that? Funny how my mind immediately focused on that. Kev guided me to the bed and we lay down together. He stroked my face and stared into my eyes. "So, my little lover, let me acquaint myself with your rear. You have no idea of the joys of the ass, do you, Raylynn? You don't know what you've been missing..." Kev peeled off my remaining underclothes, fondling each new area of bare skin, including little kisses. Oh, I felt so special, still hard and leaking but even more than that, the attention was mesmerizing. Finally he put me face down on a towel on the bed but pulled my hips up so I was on my knees with my head down. "You liked sucking me, didn't you, Raylynn?" "Yes, it was intimidating at first but sooo sexy Kev." He pushed two fingers in my mouth and moved them in and out. "Suck. Good girl. You'll get the real thing soon enough." I was rotating my hips as I sucked his fingers, feeling like a pure slut - naked on the bed, my ass sticking up and an equally naked man shoving his fingers in and out of my lipsticked mouth. I'd been hard so long now I was almost in an altered state of consciousness, mindless of anything but sex. Kev pulled his fingers out, sucked them himself and moved to my rear. He reached down and brought a bottle up, then pumped a thick liquid onto the top of my ass. He slowly spread it around my globes and into my crack then pumped more into his hand. I was moaning and whimpering as he continued to gently massage the thick lube into my upturned ass. He reached down and played with my balls which were hanging down below, briefly stroking my cock but immediately moving back to my ass. He brought both hands into play, spreading my cheeks and moving into towards my quivering hole which he teased with his thumbs. Running his fingertips over my hole, pressing onto it lightly without entering, Kev said, "This is what eroticism is all about, Raylynn. Not a quick fuck and a cigarette, and not two hairy men pounding each other. Slow, maddening, teasing, probing, wet and delicious. Do you agree?" "Ahh, ahh Kev, I...oh...please let me come now, please, I...oohh..." I was incoherent, just babbling, pushing back against his fingers and hands, rotating my hips and luxuriating in the decadence of having this man tease and probe my virgin ass. "Ha! Thought so. Deep breaths, relax." He kept at it, more teasing and stroking. "Do you want me inside you, Raylynn? Tell me." "Yes! Yes yes yes! Please Kev, please, yes, now, fuck me please!" Kev finally took pity on me and got behind me. He spent another few minutes teasing my ass with his cock, rubbing it up and down my crack, underneath my balls, but then eased it in. Yes, of course it hurt but not for long (as I'd been practicing with my toys), and soon he was slowly pushing in and out, about half of his length buried in me. Oh my god...it felt wonderful after the initial shocking pain. I felt complete somehow, feeling him inside me, knowing that I was fulfilling my man, even my destiny. Oh, it was so good... "Yes, further, please Kev, push it in all the way." Ever the gentleman, he did just that, pushing in completely. I could feel him push against my special spot, so deep, and I leaked even more. It almost felt as if I was coming continually as he pushed in and out, massaging my thighs and ass, pinching my nipples, pulling my balls as he kept up a steady rhythm. After a few minutes he started to really push, faster and deeper. I pushed back hard on each stroke and he yelled out as he smashed into me, over and over, hard as he could, releasing into my ass, all the way in, scratching my back and thighs as he spasmed against me, draining himself. He pulled out slowly, turned me around and lay full length on top of me. We kissed gently. "Oh Raylynn, that was wonderful, thank you. And thank you for trusting me as your first." Kev made me feel so special! Kev moved down and took me into his mouth. I wasn't even sure at that stage if I had come with him inside me, but he quickly coaxed out a full load while massaging my balls. We shared my leavings in another kiss. ******** Next weekend, Kev invited me over to stay. I was thrilled, two nights with Kev! I had no idea it would turn out much more than the two of us. We met on a Friday after work at his house and spent a lovely evening eating, drinking and in bed. Kev introduced me to a lot of new positions and he helped me continue to become a woman for him. I'd waited all week for this and I wasn't disappointed - the opportunity of being with Kev was the greatest incentive I've ever had at work. On Saturday morning, however, he announced that he had an appointment and that I would be welcome to help. Turns out that the 'appointment' was in his house. He refused to tell me what it was about but that I was to wear my best feminine clothing, basically bedroom wear. Kev had bought me so many lovely things it was embarrassing. Panties in sexy colors of different styles with matching bras, nightgowns, so many shoes, and everything else including loads of expensive makeup and wigs. The pantyhose were superb and I couldn't wait to try them on. I spent a long time bathing and shaving and moisturizing, wanting to be perfect for Kev. But what type of appointment was this? Why would I need to be in bedroom clothes? Was Kev some sort of pimp or what? "Just trust me Raylnn. If you're uncomfortable I'll immediately sort it out. I just want things to be perfect for you, but you need to have an open mind." We were in the living room, me in my finest with a sheer nightgown covering my pale pink barely there panties and matching bra, strappy high heels and a long blond wig. I had done my nails, hands and feet, and felt (and smelled) delicious. The doorbell rang and Kev, in very tight pants and his ever-present compression shirt, opened it to a lovely woman. She was about 5'4", straight black hair, and curves to die for. I was so jealous! Kev kissed her on the mouth, while they hugged in a very sensuous greeting. Finally they peeled away from each other and the woman turned to the still open door. "OK, you may enter, Evie." I thought, WTF?!? 'Evie' was a tall, fit man, nearly as tall as Kev, and looked like an athlete who had started to let go. Still muscular but tending towards fat now. How could I tell? Evie was wearing a crop top which showed his somewhat pudgy midriff, along with painted-on shorts that fully outlined his large rear. He had little white socks with pink bows and pink shiny shoes with short heels and silver buckles. Adorable but very disconcerting on Evie, who was very obviously a man, even with his short bobbed brown wig and makeup. Probably late 30s or early 40s, Evie looked, well ridiculous. I don't think that he could pass as a woman even in suitable clothes and subtle makeup, but in his nighttime, almost whore-ish makeup and little girl outfit, well, I wasn't yet sure what was going on. The woman, Stacy, was introduced to me by Kev. "Oh Raylynn, I did hear about you but you're so much lovelier than Kev mentioned! I so happy to meet you." We air kissed and she spun me around. "How do you do it, Raylynn, you're so pretty and yummy!" Stacy took the liberty of squeezing my ass and even my breasts. "You are perfect! Come here, Evie, I want you to meet the lovely Raylynn." Evie looked uncomfortable, to say the least. He was blushing and kept tugging at his shorts which seemed to be creeping up his crack almost like a thong. He was hairless below his head as far as I could tell, but seriously, he'd never pass so what was the point? "Pleased to meet you, Ma'am," Evie said to me breathlessly, in a sort of strangled attempt at a high-pitched voice. "I love what you're wearing, Evie. It really highlights your fantastic figure!" Stacy laughed at that. "Evie has lost a lot of weight but still has some way to go, don't you, Evie? She needs some encouragement however and meeting new people looking not as slim as she'd like helps, doesn't it, dear?" Evie immediately answered, "Yes, Mistress, you are correct, I do need to lose weight. Thank you for taking me to meet your friends." He'd obviously been coached and seemed frightened to say the wrong thing. What did Stacy have over Evie? We sat down on the couches and I brought iced tea for everyone. We chatted about inconsequential matters until Stacy said, "So, Evie, let's get started, shall we? Kev, thank you so much for agreeing to teach Evie how to please a man. I can only do so much with her, even with strap-ons and other implements. Evie needs a real man to teach her. Let us begin." What?? I must have looked astonished as Kev quickly said to me, "It's OK, Raylynn. See, I'm sort of a part-time social worker in addition to my usual day job. I help young women such as Evie adjust to their, um, new circumstances on behalf of their better halves." "Oh, Raylynn, didn't Kev tell you? Kev's such a lovely man, he's agreed to help me train Evie. Kev is very well known in certain circles as the man to go do to help with partners who need to move to the next step in their training. After all, it's so much better, more kind and safer, than to just push them into the arms of some random big bear who would choke the poor sissies with their massive cocks and rape them. Don't you think so, Evie?" "Yes, Mistress, I'm so grateful to you and Kev for training me." Evie looked anything but grateful - he looked somewhere between apprehensive and terrified. Kev stood up and walked over to Evie. "Unfasten my belt." Evie looked up, Kev's crotch in his face, and fumbled with the buckle until he could pull the belt free. "Now unzip and pull down my pants." Evie struggled to pull the tight trousers off but managed to get them down, leaving Kev's very impressive bulge sticking out of his skin-tight, semi-transparent panties. Evie just stared at the bulge in front of him. Kev turned around and bent over slightly. "Touch my ass, Evie. Feel my tight globes through the material." Evie visibly gulped and reached out, very gently and tentatively caressing Kev's rear. I was jealous of this big sissy but felt obliged to help. "Here, like this Evie." I took her hands and placed them solidly on Kev's perfect ass and pressed down, rubbing in small circles, moving Evie's thumbs into the crack. Kev rotated his hips. Stacy meanwhile was practically drooling, tearing her eyes from Kev's backside to Evie's face. She reached down between Evie's legs. "Evie, oh, you like Kev's ass, I can tell, your little cock is so hard, much harder than it gets for me. Reach down and touch his balls, yes, those huge, smooth balls in their sack. Doesn't it make your mouth water, you big sissy? Lean forward and put your nose there, yes, like that - sniff. Can you smell a real man? Not like my toys, is it? Smell his arousal, Evie. Does it turn you on?" It certainly turned ME on! I so wanted to be where Evie's face was, licking and sucking and...mmm! But I needed to go back to being helpful. "Let's, uh, move upstairs now, shall we?" "Oh Raylynn, you're a dear," Stacy exclaimed. "All hot and bothered. Should you and I do something about that together while the men play? I'm so juicy, do you want to feel?" She was rubbing her crotch and staring at my own crotch, pointing obscenely underneath my panties. "No, Stacy, I need Raylynn to help with my, uh, social work with Evie. Let's all go upstairs." We quickly decamped up the stairs. Luckily I had changed the sheets and freshened up the room this morning. We walked in and Kev turned to Evie. "Evie, you need to be more than a receptacle. You need to create desire. The sexiest women don't just assume that they can just lie back and spread their luscious thighs, they tease, tantalize and play, make their men so hot that they can't possibly refuse the charms on display. They use all their skill to entrap their men and make them crazy with lust. Now seduce me." Evie looked confused and walked to Kev then immediately started to fondle his bulge. Kev laughed. "That's one way I guess. Raylynn, perhaps a demonstration?" I walked over to Kev, gently pushed Evie aside and stroked his face with both hands. I licked my lips, slowly, then licked his ear. I pinched my nipple through my bra then pushed that finger into Kev's mouth. "Suck, Kev. Oh, that's nice." I took my finger out and pushed it into my own mouth, took it out and drooled on it a little, then caressed Kev's nipple with the same finger (as he seemed to have lost his shirt during the walk upstairs). I pushed my hips forward and rubbed our bulges together briefly then pulled away. I pinched both of Kev's nipples, tweaking them, then reached around and grabbed his ass, pulling him into me hard. I kissed him, frantically, pushing my hard cock into his, attacking him with my tongue, then quickly pulled back, pulling his hair and moving his head away from me. I sucked on his neck, put my hand between his legs and underneath him to caress his balls through his panties, then pulled back. "Oh Raylynn, that's, oh...good demonstration! Now try Evie," Kev panted, and sat down on the bed. Stacy was already there rubbing herself again, having stripped off to her underwear and bra. She attacked Kev, pulling him down on the bed, but Kev quickly pushed her off. "Please my dear, it's all about Evie today." Stacy pouted but turned her attention back to her partner (husband?) who was standing open-mouthed, his cock tenting his own panties. I sashayed up to him. "Do you like me, Evie?" I breathed into his ear from behind, pressing myself into his back. "I love your ass. Does this feel nice?" I pushed myself against him, into his crack, and caresses his inner thighs. "It doesn't always need to be brutal. I bet Stacy rapes you, am I right?" I kept whispering in his ear as I undulated against him, swaying, almost dancing with him, pressed into his large ass. "I like it slow, sensual, wet and dripping, slowly oozing. My cock is leaking. You want a little taste?" I pulled away, reached into my panties, rubbed the head of my cock and pulled my fingers out. I pushed against Evie again and put my finger near his mouth. "Lick it, Evie. Taste." Evie stuck his tongue out and gave my finger a little lick. "Suck it, Evie." He was well trained and did as he was told. I moved my finger all over inside his mouth as if it were my tongue, then pulled it out with a small plop as he sucked. I spun him around and kissed him - very gently. He tried to attack my mouth but I grabbed his hair (careful not to dislodge his wig) and pulled him back. "No silly, I make the rules, you don't get to do - you're a sissy remember!" I bit his lip as I traced his backside with my fingertips. "Raylynn, the poor girl will explode! As I will from just watching! Now Evie, rest for a minute, here, lay down on your belly, relax." Evie did as he was told and lay on the bed on his front. Kev quickly pulled his hips up. "On your knees, head down, that's it, I don't want you to hump the bed, you dirty girl." Kev and I worked Evie together - oiled her ample rump and teased and prodded her, stroking her oily, hard cock, caressing her low-hanging balls and teasing and penetrating her hole. Evie was close so we had to be very careful not to end his agony too soon. "You want me inside, don't you, Evie? Let's see if it fits, shall we?" Kev kneeled behind Evie and teased his hole with his cock - up and down his crack (spreading his ample cheeks wide), then finally slowly fitting the head inside. I was up front sitting near his head. "I know what would help, Evie! Take a look, my toenails are wonderful, don't you think? With Kev's hard cock moving up your virgin ass, it's the perfect time to get your mouth busy - here, suck on these! That's it, give them a good lick, then suck each toe - yes, like a little cock! Adorable watching your face - don't worry, it won't hurt for long, now get your mouth busy, sissy! You're here to give pleasure remember..." Evie was slobbering over my toes and Kev was ever the gentleman, pushing in slowly then stopping, letting Evie get used to him invading her back passage. I decided to try to be a bit more helpful, extracted my soaking wet toes and lay down close to Evie. "I know it's uncomfortable at first, but relax - deep breaths. Yes, deeper and slower, like this...see? Yes, copy me. Deeper and slower...yes, that's it. Relax your ass, stop trying to block him, let him in. Push out, don't clamp down. See? I can tell it's better, yes? Keep breathing, don't stop. Think about what's going on - you're lying on a bed with your naked ass up in the air, wearing women's lingerie, and a big, strong man is fucking you. Yes, his long, hard cock is up your ass, right now! Exciting, yes? Feel it go in, all slippery and slimy, as Kev holds onto your hips. Kev, give his ass a few slaps - feel that? Gorgeous, right? Starting to feel better yet?" Evie was sweating profusely, but at least his face wasn't dangerously red now. I stroked his back and his flanks and kept telling him to relax. I signaled to Kev to stroke poor Evie, at least until he got his mojo back. After a few minutes it was working, and Evie was even very gently pushing back against Kev. I could just imagine Stacy pounding Evie mercilessly with a giant strap-on, raping him, and I was determined that this was going to be an enjoyable, even loving, scene for him. What he saw in Stacy I couldn't fathom other than she was clearly highly sexed and had a jamming body. But still, I wouldn't let anyone order me around like that. Or would I? I leaned over and kissed Evie, gently, trying to give him a bit of love. He was starting to respond now, and I ventured underneath his to make sure that he was having a good time. Kev was moving steadily in and out and I couldn't help but give him a bit of love first, fondling his gorgeous ass moving back and forth, then his balls. Evie wasn't erect so I took his soft member into my mouth and coaxed it to life. He was quite big and surprisingly thick. And, well, yummy! It was after all only the second one I've had, and tasted great. I had him hard quickly and stopped, I didn't want to have him spurt prematurely. I moved back to his face and we shared a kiss. "Can you taste yourself, Evie? You're delicious, don't you think? Kev's really working you over now. I can see you're enjoying his cock in your sissy ass. It's nice, isn't it? And it just gets better. Now you can return the favor, see if you like mine." I scooted around, spread my legs and to his credit Evie immediately took me into his mouth. He was enthusiastic but inexperienced - still, I had no complaints. Up and down he bobbed on my cock, I was going to lay back and enjoy it but Kev signaled me to hold off. I reluctantly pulled away and kissed him again, just to taste myself on him. He did sweat a lot, our Evie! Definitely needs more gym work and to lose his baby fat. Kev started to really move just then, pushing much deeper, really pounding each stroke. Evie gasped each time, whimpering and squeaking as Kev worked him over, holding his hips while slamming into his virgin ass. Stacy must have come 5-6 times - she had practically her whole hand buried in her snatch. "Yes, Evie, your dream come true at last, a big hunk fucking your ass with his hard cock. Pound it into him, harder, Kev!" She was clearly jealous but enjoying it all the same. I decided to give Kev a helping hand and stood behind him, pressing myself into him as he pummeled Evie. I took a step back after a few minutes, spread his legs out and rubbed his balls and ass. He slammed even harder into Evie, who was making loud, 'aaahhh!' noises on each stroke. I managed to get a finger or two into Kev's pounding, squirming ass, and it was enough - he pulled Evie in close and let rip with a growl. Kev kept it up longer than I had thought he would, really emptying himself inside Evie. Stacy was clearly coming as well, practically screaming. Not to be outdone, I quickly shifted back to Evie and stroked myself, coming all over his face in record time. Phew! We all needed a breather. I fed my come from Evie's face into her mouth and then we had a loving, sloppy kiss. Kev pulled Stacy's legs up, spanked her for a few minutes then roughly rubbed her then quite brutally fucked her with most of his hand until she came again. Evie and Stacy left, but not before I whispered to Evie that he was welcome over again, preferably without Stacy. He seemed to be shocked at the suggestion but nodded in agreement. Kev and I cleaned up and he told me that he offered this type of service for women who were training their husbands in the feminine ways of the world. He called it his 'social work' and was very pleased with my assistance. Funnily enough, the next weekend was already booked for another couple - can't wait!