22 comments/ 40767 views/ 42 favorites The Roommate Ch. 01 By: Cordellia I had only just moved to the city, moving into an apartment with my best friend from school, Ryan, when he had got a job offer in another city. Ryan hated his job and the offer was too good to refuse, so he had to go - and I had a month to find a new flatmate. But three weeks passed, and still no one replied to my online flatmate wanted ad. I was starting to get concerned. That was until I got a text from Monica. I wasn't sure if I wanted to get a girl in - what if it got awkward? I've got a long track record of getting it wrong with girls, I've often got the wrong message and ruined many good friendships with women because of this. Nonetheless, I desperately needed someone else to move in as I wouldn't be able to afford the rent by myself, so I invite Monica to check out the room. The following day, I spent all morning cleaning the house, wary that no one woman would want to live in the pigsty Ryan and I had happily called home. The doorbell rang just after midday, and I rushed to the door, stubbing my toe on the vaccum cleaner I had failed to put away. Shit, I murmured to myself, chucking the vaccuum cleaner behind the door. The door bell rang again. I opened the front door and felt the air sucked from my lungs. Monica was gorgeous. Her shoulder-length black hair framed a soft face, her eyes dark and her lips a rich red. She wore a black dress, low cut, her pale arms exposed. Her legs wrapped in black tights, her feet in stylish ankle boots. Immediately I knew I would fall for her. "Sorry I'm late," she said. "Hey, you're not at all, come right in." I showed her around the house, her room, the living room, the kitchen, the bathroom. She said it was what she was looking for, close to town, decent sized, a lot of natural light. She had only just moved to the city, and was looking for a new job and new friends. "I've just got out of a long relationship and I figured I needed a new start," she told me over coffee on the deck. "It will good to meet new people and move on from the past." I told her I was new to the city too so we're in a similar situation. Monica moved in one week later. We hit it off quickly, sharing a lot of interests and she got my sense of humour. After a few drinks one Friday we started talking about past relationships. "So did you have someone in your last city?" She asked. I told her I'd been single for a few years, apart from a few one-night stands I'd struggled with women recently. Shit, I'm hardly playing it cool, I thought, so figured I should change the subject. "How about your last relationship, if you don't mind me asking?" "It's alright," she replied. "We were in different stages in life, we wanted different things. I wanted to travel, go to new places, while she was settled with her job and was keen to stay where she was." Did she just say she? "She?" "Oh, yes, she, I'm a lesbian. I hope that's not a problem?" "Oh, no, that's fine. Perfect in fact." "Perfect? Um, why?" She seemed uncomfortable. "Oh, no, not like that. It's just, well..." "Well what?" "Well, when I first saw you I thought you were gorgeous. And I had hoped you wouldn't be." "Why?" "Because I didn't want to fall for you. I needed a flatmate and I wanted us to get along, without me falling for you and ruining everything. But I think now I might have made it awkward anyway!" "Of course you haven't," she reassured me. "I'm used to having attention from guys, and having to let them down. You're such a sweet guy I'd hate things to get awkward with us. I know I've only known you a short time, but I feel I can really trust you. I can see us becoming really good friends." "Glad to hear it." I was relieved. I really didn't want to have to find another flatmate, and Monica had become a good friend - and I didn't have many of those in the city. The next night, we were having a few wines together again. We didn't know many people and it was cheaper to drink at home. Monica was wearing the same black dress she'd worn when I first saw her. "I like that dress," I told her. "Thanks," she responded. "What do you mean you like this dress? You know I'm gay, right?" "Oh, of course! I mean you look great in it. It was the one you wore when you first came here, and you looked gorgeous. Sorry if that across weird, maybe I've had too much wine!" "No no, sorry for taking it the wrong way, thanks, I'm rubbish at taking compliments. It's my favourite dress, I'm glad it suits me." The room went quiet for a moment, a weird tension remaining after my awkward compliment. But it was only to get more awkward. "Would you like to try it on?" "What?" "The dress, would you like to try it on? I mean, if you like how it looks on me, I'd like to see how it looks on you." "Why?" "Because it would be fun. Have you worn a dress before?" "No," I lied. "You've got the figure. I mean that as a compliment." It was a weird compliment. Monica and I had similar builds, not too skinny, but slim. "Alright, let's put it on then." "Wow, you're easily convinced. Alright then, girlfriend." She unzipped the back and dropped the dress to the floor. She stood there in the middle of the living room, exposed apart from her matching maroon bra and panties, and looked up at me. "What are you looking at?" "Nothing, sorry." "Well take off your clothes." I lifted my shirt off and wiggled out of my jeans. She stepped out of her dress, and kicked it up at my from the floor. I awkwardly stepped into the dress, and pulled it up. Monica reached around behind me and zipped it up. "Fits perfectly. A little too well. You've even got the hips for it. But you're a bit bare up here," she said, fondling my chest. "We'll have to sort that out," she said. She went to her room, leaving me standing there emasculated in the living room. She returned with a padded black bra. "Really? I'm not wearing that!" "Come on, you look silly otherwise." "I'm going to look sillier with it." "Rubbish." I relented, lowering the dress from my shoulders so Monica could put on the bra. She slipped in some extra padding to give me two modest breasts. "Perfect." "Perfect? I feel stupid." "Well that's only because I haven't done your make-up." "No no no, that's not happening!" "Please! It's just you and I, no one else needs to know. It'll be fun. Don't you trust me?" "Of course I do. Fine then." She led me into the bathroom and sat me down on the toilet seat. She grabbed her bag and worked away at my face, pointing pencils here and brushes there, ordering eyes closes and mouths pouted. She then reached for another bag, and pulled out her hair straightener and set to work with my hair. My blonde locks are long for a guy's, so it wasn't hard for her to work it into a woman's style. She looked me up and down. "Something is not right." "Really?" I said sarcastically. "Where do I start?" "Ha ha. No, I know what it is. Can I please shave your legs?" "No way! I'll look ridiculous." "No you won't. Besides, summer is months away and if you bring a girl home say you swim or cycle or something." It wasn't likely I'd be bringing a girl home any time soon. Bugger it. "Alright then." "Wow, you really are game tonight!" She lathered up my legs and set to work. She went up passed my knees and up my thighs, lifting the dress as she went. Her hands on my inner thigh got me aroused, lifting the dress higher. "You're really enjoying this, aren't you?" "Hey, how am I not meant to get excited with you up my dress!" She then got my to lift my arms, and removed the tufts from my arm pits. Once done there she stood up, stepped back and admired her handiwork. "A few more things." She darted back to her room, returning with a couple more items of clothing, and a pair of heeled black ankle boots. "Put these on," she said, handing me black panties and a pair of tights. I didn't argue, I'd gone so far already, what more is a pair of panties and tights. I slipped on the panties and lifted the tights up my legs. She passed me the shoes and slipped my feet in. They were tight, but Monica and I were remarkably similar in size. "You look gorgeous." "Really," I again said sarcastically. "No, really. Look." She lifted a mirror to my face. "Wow." Looking back at me was a beautiful girl, with dark eyes, rich red lips framed with shoulder-length blonde hair. "I look ..." "Hot. Sexy even. And I'm qualified to say that," she laughed. "Come to my room and look at yourself in my full-length mirror." I followed her to her room and stood in front of the mirror. I had thought I'd look like a man in drag, but no, I was gorgeous. "You're really gorgeous," Monica said, quietly in my ear. "I know." I gulped. "I hope you don't take this wrong way, but you're a better looking girl than a guy. Like, you could get anyone you wanted looking like this." "Um, thanks, but I'm not gay." "Are you sure? You're the one dressed like a woman." "Haha, very funny." "Come on, let's go watch TV." "Um, I'm going to get changed first." "Why? You're so pretty. Come on, stay dressed up for a while. We can hang out as girls this evening." "But I'm not a girl," I protested. "I wish you were," she said. "Come on." I followed her onto the couch, and we both slouched down with our feet balanced up on the coffee table. What had she meant by 'I wish you were a girl'? Is she turned on by me looking like this? Yeah, she's gay - but I'm a guy. Monica flicked through the channels, settling for a cheesy chick-flick. "Perfect movie for a girls' night in." I said nothing, still trying to get my head around the situation. Why was I dressed like a woman? And what did Monica mean earlier? I had to admit, I was surprised by how good I looked. And I was secretly enjoying the feeling of the tights on my legs, the bra strap digging lightly into my skin, the slight stickiness of the lipstick. I know it wasn't right, but it felt so right. Monica leaned her head on mine, and slid her hand into mine. "I wish you were a girl," she said once more. She leaned in and kissed me on the lips. The Roommates Ch. 01 I haven't written many stories at all so far, but this is definitely my most adventurous. This is your fair warning, read the category this one has been submitted to. The Roommates Ch. 01 Daphne was suddenly everywhere, all over him, smothering his mouth with hers, holding his head in her hands and then sitting on his lap, grinding her crotch against his. His soldier rose to the occasion, knocking on her door. She quickly unbuttoned her top and pulled it open to reveal her beautiful breasts encased in a lacy white bra, with a healthy amount of cleavage on display. Brad buried his face in it, his tongue slipping from his mouth to lick every square inch of breast flesh he could reach. It had been a while for him and he was more than ready for whatever Daphne was offering him. He felt her bra go slack, and before he knew it she was totally topless. He leaned back to admire her pale breasts; she was very fair skinned. Her areolas were quite small really, only about the size of a twenty cent piece but they were really puffy, and her nipples were rock hard and stuck out about 12 or 15mm, being about the same size around. He latched onto her left one, opening his mouth wide enough to suck in her entire areola. His tongue worked her nipple, wrapping around it and pushing it all around, up, down, left and right, trying to twist it around. He pulled his mouth off until his lips were wrapped around her nipple and sucked hard, gently biting with his lips. He'd always been obsessed with breasts, ever since his first erection. Before he was finished, before he'd even considered moving on to the next nipple, Daphne was up off him, and for a moment Brad felt disappointment, before she reached for his hand and with surprising strength pulled him after her as she headed for her room. He didn't have long to take it in, beyond thinking, 'she's into sport' as he noticed a few posters. She dropped to her knees in front of him, attacking his belt and reefing down his pants along with his boxers, allowing his cock to spring up into her face. It was like she was possessed; she didn't even say anything, just started slurping, licking, and sucking on his pole. His head rolled back in ecstasy. Her soft lips surrounded the head and massaged the ridge, while the tip of her tongue drew circles around his slit, before lightly probing it. After half a minute or so, she worked a little lower taking a few inches and bobbing back and forth. Her tongue circled the head of his cock, caressing it. She ran her mouth and lips back and forth, slowly, lovingly sliding her lips back and forth on the shaft. She began taking a little more on each bob, and Brad watched as she easily took more than anyone he'd ever been with. He considered himself to be bigger than average at about 7 ½ inches, nothing too amazing, but no-one had ever swallowed as much as Daphne was, and she seemed to be doing it easily. Brad was getting really worked up watching her blow him, and started to rock his hips back and forth. She gripped his arse cheeks, the tips of her fingers sliding into his crack, and she used her grip to control the tempo. When he felt her nose brush his stomach he was ready to blow, but she sensed this and paused, with his cock completely buried in her mouth and throat, calming his impending ejaculation. He could feel the start of her throat halfway along his cock, forming a grip around his pole. Slowly, she extracted herself from his cock, and stood up. "I've got somewhere even better for this thing." She turned around, and reached back for the zipper on her long skirt. She unzipped it, and shimmied her hips out of it, dropping it to pool at her feet. She looked back at him coyly over her shoulder. She was now wearing nothing but a lacy white thong, with a thick waistband. Brad's impressions had been correct, she was very slim, and lithe, her hips widening from her waist only slightly. Her bum was surprisingly pert and tight, and he was filled with the urge to grip it in his fists while ramming his dick inside her. She raised a knee to the end of the bed and kneeled upon it. Still looking back at him, she produced a tube of lube from somewhere, while her other hand pulled her thong to the side. She began lubing herself up, "How'd you like to fuck my arse Brad?" Brad was all up for that. He'd had anal sex a couple of times before, but never before had a girl offered her arse to him like this. He pounced on her and she squealed. His prick slid up between her arse cheeks, rubbing in some of the lube she'd smeared around, and nestling snugly between her tight buns. He reached around to grab a hold of her big titties, as her nipples pressed into his palms like hard little pebbles. They felt divine in his hands and he hefted them around, rubbing the rubbery nipple and eventually taking hold and squeezing them a little, along with a light twist. Meanwhile he slid his meat back and forth up and down her rump, while the breast play had Daphne joining the action, shaking her arse up and down against his dong. "Don't tease me Brad, stick your cock up my arse already," she said, handing him a condom. Brad wasn't one to disappoint. He reached between them and took hold of his joystick and quickly rolling the condom on before lining it up with her cute little pink arsehole. He applied a bit of pressure and watched her little rosebud blossom to accept the bulbous head. "Oh fuck baby, yes, stick that dick up my pussy... my ass... just stick it inside me." She'd lubed up well, as he just slowly slid inside. She took the whole thing without a worry. It felt fantastic. Instead of pressure along his entire cock, which is how a pussy felt, Daphne's arse applied a tight ring of pleasure around the base, while the rest was just lightly tickled. He pulled back through the ring of pleasure and groaned in ecstasy. The other times he'd had anal sex it had been really awkward and painful, but both Daphne and Brad were instantly enjoying it. He pushed back inside firmly, causing them both to huff with effort. "Yeah baby, fuck that arse." Her cute little butt looked so sexy as he shoved his cock in and out of it. He was now gripping her hips, marvelling at how fit she was, feeling strong muscles flexing. He was sure his dick had never been so hard in all his life. It had been a long time between bouts in the bedroom for him, and he certainly hadn't had a chance to jack off in a while, so he wasn't surprised when he felt the rumblings in his balls announcing his imminent ejaculation. He felt bad though, Daphne was awesome and he didn't want to disappoint her, or let he think he was a bit of a dud. "Oh baby, your arse is so tight, so fantastic, I'm not going to last much longer here," he said between panting. "Fuck I'm horny, shoot it on my arse, baby. Shoot your batter all over my arse, paint it white baby." Brad pulled out of her arse and ripped the condom off. With only a couple of jerks he was erupting, spurt after spurt. It started up her back, before he aimed his dick at her arse cheeks, giving each a nice glaze. "Shit yeah honey, rain that goo all over me." With nothing left, Brad stood behind her catching his breath. He looked around for something to wipe his cum off with, but was interrupted by Daphne, "Thanks Brad baby, that was great. I really needed that." "No problem," he replied. "Well, I'll see you later then. Maybe we can do this again?" She was obviously dismissing him from her room. Embarrassed, he grabbed his pants and backed towards the door. "No problem Daphne, thanks..." He closed the door and leaned against it. Immediately he could hear Daphne moaning in there. He was completely confused, if Daphne wasn't finished, why was she kicking him out? He wasn't finished, sure he'd cum, but he could go again, and he had other skills. It was very emasculating, and probably the strangest feeling he'd ever had. He wasn't one of those guys who just dismissed girls after they'd gotten their rocks off, but he wondered if this was how such girls felt after being kicked out. He didn't go to sleep with a hard-on that night, but he was very confused, and worried about what Daphne thought of him.