By Christmas, Sarah and I had been ‘dating’ for a few weeks. If you could call it that. I had been spending a lot of my time with her, but I often felt more like a servant than her boyfriend. Most couples might curl up together to watch a film, I was more used to curling up at her feet. Worse, I was sure my friends realised there was something odd going on. Mark, who had the room next to mine often smirked knowingly at me. The others were always a little cold around Sarah and had started treating me differently.
The weeks had gone by in a sexual haze. I’d knelt between her legs to service her with my tongue more times than I could count. I’d feel her hands slip down the back of the panties she made me wear whenever she wanted to arouse or embarrass me. Once, I spoke sharply to her in front of my friends. It was a movie night and to get back at me she wrapped her arm around me under our blanket. I had to quickly suppress a moan when I felt her start to finger me right there. I then spent the next hour trying to remain silent, trying not to cum in my silky panties and mostly trying to ignore the feelings this girl created in me, seemingly unaware of my embarrassment. When we went back to my room, she had me lie over her lap for one of the many spankings I’d received over the weeks we’d been together. I was sure my friends heard them, I’m now certain Mark did.
In Mid-December, My housemates planned a party for Christmas and we’d decided to do a Secret Santa. Somebody suggested that one of the group should dress as Santa to give out the gifts people had been bought. I had no idea why at the time but Sarah immediately volunteered. The others laughed but suggested that I should do it instead. My heart sank as Sarah told them it would be fun and that I could be her beautiful assistant. I knew then this wasn’t going to turn out well for me.
I wasn’t wrong. On the night of the party, Sarah showed up dressed like a perfect, traditional Santa. She was a little too slim but she’d even found a false beard to give her some authenticity. My friends loved it and asked about my costume, only to be told to wait for the surprise. Sarah then dragged me to my room and stripped my clothes off, right down to the white and pink chiffon thong she’d left the night before. She hadn’t explicitly told me to wear it that day, but I’d known better than to ignore panties she’d left in my bed.
“Oh you’re such a good little boy.” She murmured, cupping my balls through her thong. “You always know what to wear to make me happy. Will you wear something special for me today? Maybe if you make me really happy, I’ll make you happy when the party is over…”
I moaned and just nodded, feeling her fingers trace further between my legs. I’d lost count of the number of times she’d hinted at sex to make me do things. I knew I shouldn’t believe her but something about the way she spoke was irresistible. Her fingers followed the material of my thong and I could feel her putting pressure between my cheeks; teasing me. Her free hand rummaged in her bag and eventually she handed me a pink box.
“Go shower and use this sweetie. No hair below your eyebrows and then you can try on your costume!”
I looked at the box and sighed, it was hair removal cream and I was terrified by what she had in store for me.
An hour later, the party was in full swing and I had a red velour dress on; greeting people as they arrived. Not just any old dress, a tiny red dress. The fluffy white trim of which barely covered my red lace panties. I was dressed as a slutty female Santa, complete with candy striped hold-up stockings and bright red heels. My matching gloves went to my elbows but barely covered my hand, so Sarah had given me long, red, false nails. Everyone laughed when they saw me but only in good fun. They seemed to think it was hilarious and complimented me on how I looked. Some even seemed a little too flattering! Only my friends, who knew Sarah quite well, looked more worried than amused.
I was embarrassed but the good cheer stopped it being too humiliating. The only problem was Sarah, she wasn’t paying much attention to me. She even seemed to flirt with the other guys at the party, the ones not wearing slutty dresses. She finally pushed it too far when it came time for Secret Santa. At first people jokingly sat on her knee to tell her what they want for Christmas and be given their present. I stood to one side, smiling and organising everyone. Everyone laughed each time some joker groped the Sissy Santa (as Sarah took to calling me) and I tried to hide my reactions; the growing shame and occasional stirring in my panties. Eventually, most people had been given their presents and wandered away. At that point, my friend Mark was called up. I led him over to Sarah, blushing when he pinched my lace covered bum.
“Well now, you’re a big boy!” Sarah did her best Santa impression. “Maybe you won’t fit on Santa’s knee.”
Mark laughed and suggested she’d be more comfortable on his. I wanted to protest but she just jumped up and told me to lead Mark to his seat. When I helped him settle, Sarah immediately jumped into his lap. I was left standing awkwardly to one side as she put her arms around his neck and whispered in his ear. I was sure the arm he was using to steady her was lower than it needed to be. I started to turn red as the guests who were still there all saw them getting too close, all saw Mark’s hand holding her ass. Suddenly, she squealed.
“Oh your present!” She said, looking through her present bag. “Oh no, I’ve ran out! I must have been your Secret Santa, I forgot to get you one!”
Somehow, I didn’t buy it.
“Maybe we can make it up to you later.” She was much quieter now and looked at me as she said it.
“It’ll have to be something great, Santa can’t just give out late presents.” Mark took this all surprisingly in stride.
“You can have anything you want” She whispered and I hoped it was only loud enough for Mark and I to hear.
It was too much and I grabbed her arm to lead her to the bathroom. I could hear a few awkward laughs behind me and just hoped everyone would be gone before we got back. Closing the bathroom door behind us, I turned to Sarah.
“What the hell are you doing with Mark?” I tried not to shout.
“I’m just having fun sweetie, I know you were liking the way everyone treated you and I thought I’d just add to that. Am I wrong?”
She was so close to me as she said this that my cock started to rise, Sarah didn’t miss it and immediately started to rub the front of my panties. I knew this is why I rarely get to cum, I knew she used my constant arousal to control me but I did nothing to stop her. She turned me around and rubbed my cock with her palm, her fingers cupping my balls. I was now staring at myself in the bathroom mirror, my short skirt around my waist.
“Don’t you like looking this pretty?”
I nodded, I had to admit I did. My make up was slutty but perfect and the wig Sarah got me was long and beautiful. I’m slim (Sarah had been controlling my diet more and more as we dated) and my hairless body had never seemed so sexy before.
“And you liked how the boys treated you differently to normal? Even the ones who felt your pretty little bum?”
I bit my ever-so-red lip and nodded again. Sarah smirked and moved to feel my ass.
“You have to understand then sweetie. Part of that is men like Mark, real men, will see me and you together and think there are two girls for the taking. If you were big and manly, he’d see me with you and know I was off-limits. Instead he hears the spanking at night and just knows I’m not over your knee. He sees you in that dress and wonders if either of our asses are off-limits.”
I’m stunned, it all made sense but I just couldn’t accept it. Some part of me wanted to resist and tell her I was a man. Another just wanted to cry but as I felt the familiar sensation of Sarah’s fingers inside my panties, I knew all I really wanted is for her to never stop touching me.
“That’s a good boy, just accept it. Why don’t you slide your hand down your cute dress and pinch those nipples for me?”
That’s when Mark walked in. He saw me leaning over the bathroom counter, playing with my own nipples whilst Sarah fingered my ass and rubbed the front of my panties with her hand like she was playing with her girlfriend’s pussy. He just laughed and walked out.
“Do you want to cum tonight?” Sarah asked me just as I was on the verge of tears.
“Yes, please Sarah, you said if I made you happy, something good might happen?” I responded, I don’t know how I was so hopeful but I tried.
“Yes, now I’m going to talk to Mark. The party is over so go sit in your room and wait for me. If you do what you’re told without complaining, you can fuck me tonight.”
She spanked my ass hard and walked out, leaving me to compose myself. I couldn’t believe what she’d just told me. I thought she would never let me fuck her after the party. All night she’d seemed more interested in other guys and I thought that the last hour had labeled me a sissy in her eyes forever. I pulled my dress back into place and ran to my room, sitting on the edge of my bed just waiting for her to arrive. I wanted to strip off, be waiting for her as a man but I didn’t want to piss her off so I decided to wait for permission. As it turned out, this was the right decision.
Some time later, the two of them crashed into my room. I couldn’t believe my eyes as Sarah kissed Mark, her legs wrapped around his waist and her arms around his neck. He’d lifted her off the ground and now gripped my girlfriend’s ass in his big hands. I wanted to protest but Sarah broke off her kiss and turned to me.
“Remember sweetie, no complaints if you want to fuck me.”
They moved backwards and fell next to me on the bed. Sarah straddled Mark, kissing him passionately and I watched in horror as he ripped her Santa costume off. She was wearing a red lace bra and panty set and my heart sank as I realised they are a perfect match to my own. Mark groped her freely, her body exposed to him and I could already see the differences between myself and him. The first time I was with Sarah, I meekly allowed her to strip me whilst she ignored all my attempts to undress her. She took her dress off for me slowly and only when she wanted to give me access to please her. Mark had the roles reversed; he was fully dressed and taking what he wanted whilst she gave herself eagerly.
Her bra came off and Sarah moaned, my cock strained in my panties when I saw Mark bite and suck her perfect breasts. Slowly, Sarah slid down the bed. She motioned for me to come over and started to undo Mark’s jeans. She pulled his cock out and I was stunned. It was 8 inches; long, thick and straight. His giant, cut cock looked beautiful in her tiny hand and Sarah smiled at me and the smaller cock that was straining against my own panties.
“Get over here sweetie, there’s no need to pretend you don’t want to! You’re clearly excited and although I’m on my hands and knees on your bed in nothing but panties, I don’t think it’s me you’re staring at.”
I blushed realising the goddess I’d lusted after was in my room in a position I’d only dreamed about and I was actually salivating over my friend’s cock. I knelt beside her, shaking slightly and watched her expectantly. Sarah slowly lowered her glossy lips to Mark’s cock. I watched him place his hand on the back of her head, pushing her down as the head of his cock disappeared. Then I felt it, a large, powerful hand on my head. I leaned forward, unresisting, and kissed the side of his cock.
Sarah reached out and gripped my ass, moving to finger me even as Mark pushed my head to his balls. I licked and sucked them, reaching out to return the favour for Sarah and the room was filled with moans. Side by side, Sarah and I played with each other even as we worshipped Mark. We must have looked like total sluts, working together bent over Mark’s cock. I wondered if I should have been in his place, if I should have felt pathetic for helping Sarah but that all went away each time Sarah brought me close to the edge.
Eventually, Sarah stood up and declared she had an idea.
“If you want your Christmas present Mark, let me give you my little pet’s ass.” She smiled as Mark’s face lit up.
“And for you Sam, do this last thing for me and you will get to fuck me.” She continued quickly, cutting off my protests.
I wondered how I could accept this. She was so quickly and obviously giving Mark anything he wanted, yet I had to beg and humiliate myself just to have sex with her. Even so, the thought of finally fucking her drove me on and as I thought about it, the idea of Mark’s wonderful cock fucking me was not entirely unappealing.
I was led onto the bed and Sarah came to lie next to me, holding a bottle of lube. Mark settled at the end of the bed to watch us make out, stroking his cock. We had our hands in each other’s panties, her newly lubed fingers driving me wild and my own girlish fingers finding her soaked pussy.
“Are you excited sweetie?” Sarah smiled at me as she asked, having noticed my hips moving against her fingers.
“Yes, Sarah” Is all I could whisper in response.
“I’m getting you ready to be fucked by your friend, of course you’re excited!” she laughed and slides another finger inside me.
Mark came over and had me sit up, his cock was directly in front of me and I knew what he wanted. I looked up at him and caught his eye, sliding my lips down his shaft. Sarah shifted to sit behind me, I could still feel her fingers inside me and I was eager for something more. Knowing that ‘something more’ was in my mouth, I sucked with earnest trying to turn Mark on so he’d be desperate to fuck me. His moans filled me with a strange pride and my enthusiasm increased until Sarah spanked me hard.
“Stop that, you stupid slut! I’m sure you’re just dying for a mouth full of cum but he’s here to fuck you.”
I was shocked. Sarah humiliated me, treated me cruelly even but she never sounded so abusive. Had I really made her mad? Mark laughed and Sarah pulled me back to lie on my bed. My tiny dress was up around my waist and my panties did little to cover me from Mark’s eyes.
“Now tell him what you want.” Sarah still sounded angry.
I took a deep breath and looked at Mark. Sarah was rolling a condom over his cock,and even then I felt a pang of jealousy at her touching him. Even so, the sight of rock hard cock and the knowledge that it was me doing this to him filled me with lust.
“Please will you fuck me? I’m desperate for a real, hard cock” My voice sounded breathy and pathetic, I just hoped it turned him on.
“I can’t believe you’re such a slut! I’ll fuck you, but not like this. If you want to dress like a whore and fuck your house mate, I’m up for it. We’re doing it my way though not like some sissy girlfriend-boyfriend fantasy.”
I struggled to respond, unsure what he wanted from me. Out of nowhere, he grabbed me hard, gripping above my hips. I was pulled up into the air, my slender frame posing no obstacle to him and he flipped me over. He pulled me onto my hands and knees and I could hear Sarah moaning behind me. She must have enjoyed Mark’s treatment of me. My panties were pulled to the side and I gasped, feeling his cock pressing against my now lubed and eager hole.
Sarah climbed onto the bed in front of me, completely naked and holding a bag. She must have stripped off when Mark was manhandling me and now her fingers were buried in her cunt. She was staring intently at Mark who had started to push hard into my ass.
“Play with your cock sweetie, it’s going to feel so good once you get used to it. You just need to relax.”
Sarah sounded reassuring once again and I immediately jumped to her command. I stroked myself, letting my friend push his huge cock all the way inside me. Sarah’s eyes were glued to us when Mark grabbed my hips and started to pull out a little, truly beginning to fuck me.
“Let me help you sweetie.” Sarah said, sounding truly caring now.
She slid down underneath me and pulled my head against her chest. I sucked her nipple into my mouth and feel my hand being pushed away from my cock, only to be replaced by hers. Any initial discomfort was gone, I was truly loving being fucked by Mark. I moaned freely and rocked my hips to help him enjoy it more.
“Do you remember what you get out of this deal, baby?” Sarah asks.
I was shocked for a moment. There was more than this? More than this beautiful girl playing with my cock even when I was dressed like a slut and letting my friend fuck me? Then I remembered, I was going to fuck her. As she lay under me, all it would have taken was for her to stop stroking my cock and direct it inside her instead.
“There’s just one thing.”
I moaned, what could be wrong?
“Do you like Mark’s big cock?”
I stared into her eyes and nodded, how could she not tell?
“Don’t you think I should get a cock like that?”
I didn’t know how to respond. I could see she’s planning something but I didn’t know what. She reaches into the bag and pulls out a large, pink strap-on dildo, more like Mark’s cock than my own.
“I got this because I was going to fuck you tonight. Of course, Mark has claimed you for the night but that’s okay because I did have a second use in mind for this.”
She turned the dildo so the harness was facing me and I could see that it was hollow. My heart sank when I realised where this was going. Mark, however, was clearly enjoying my embarrassment; his pace increased when he saw what Sarah was holding.
“I don’t want to wear that Sarah, please!” I sounded pathetic.
“Oh but you do, sweetie! You don’t want to look silly in front of Mark. He’s doing a great job of fucking you isn’t he?”
“Yes, Sarah.” I could barely get the words out, Mark was fucking me hard and I was barely able to concentrate.
“So you don’t want to be writhing and moaning underneath him whilst I’m lying there looking disappointed with you!”
“No, Sarah but you won’t be!”
“Oh sweetie, of course I will! You’ll cum so quickly if I just let you fuck me and you’ll never satisfy me like that. If you wear this though you might last just as long as Mark and you’ll be able to please me with your big cock.”
I wanted to protest more but Sarah gestured at Mark and he grabbed my arms pulling me upright. I knelt with my cock pointing straight out and Sarah came forward to slide the hollow dildo over me. I struggled a little, I wanted to get up and leave but I couldn’t move away with Mark holding my arms and, if I’m entirely honest, I didn’t want to do anything to make his cock leave me. Mark stopped fucking me to take the straps from Sarah, leaving me waiting with him still inside me as he secured the dildo around me. My cheeks were burning and I couldn’t believe what was happening. With my arms free, I knew I could move away if I wanted to. Instead, with my panties around my thighs and this beautiful woman in front of me, laughing at my emasculation, I knew I should accept my role. My cock strained inside it’s pink casing and I hung my head, unable to meet Sarah’s eyes when I put my hands back on the bed and slowly started to lift my ass up and down on this real man’s cock.
“Mmm that’s right baby! Show Mark you know your place. You should be grateful I’m letting you near my perfect pussy, even with a dildo around that clitty of yours.”
I watched Sarah mocking me, furiously rubbing her clit and I moved faster on Mark’s cock. I wanted to please her, I wanted to feel more of him. Once the strapon was secure, Sarah slid back under me and started to kiss me. I could feel her grip the dildo with my cock inside it and pull it towards her.
“Fuck me, darling.” She whispered in my ear.
I pushed my hips forward and met resistance as the dildo pushed its way inside her. I could barely feel it and was crushed by how unfair this all was. Then Mark pushed deep into me. Sarah gasped and moaned, I was slammed into her and my pink dildo was buried inside her. I tried to pull out but Mark’s weight held me down. He grabbed my hips and pulled back, first pulling my dildo out of Sarah and then holding me as his cock slid out of my ass. I realised too late what was going to happen.
Mark fucked me hard, controlling every bit of movement. My strapon moved in and out of Sarah without the slightest help from me. I tried to move my hips, tried to be the cause of the moans escaping from her lips but I couldn’t. Mark was fucking both of us and even as I realised the shame of it all, I was turned on beyond belief. Here I was, slutted up in matching panties with another girl; this incredible man fucking both of us.
“Isn’t he such a stud, baby?” Sarah moaned. “He’s handling you like a rag doll and fucking both of us!”
I moaned, even the slight movement of the dildo on my cock was bringing me ever closer to cumming.
“I know you love it, you’re so accepting of your new role! It’s taken me so long to train you like this but we’re going to have so much fun together. Now take your little hands off me, you don’t need to pretend you’re the one fucking me anymore, hold that pretty ass open for your friend.”
I reached back, sinking down onto Sarah and placed my hands on my ass, holding it open for Mark. He lifted me up and pushed me back down over and over until Sarah started to claw at my back and scream. His cock slid into me faster and faster; Mark was clearly enjoying watching Sarah as she came.
Sarah collapsed onto the bed, just waving her hand at Mark. He lifted me up and away from her before pushing my head back down, fucking me hard. I could feel my strapon being removed and looked up to see Sarah putting it on herself. I was moaning in half pleasure, half pain. Mark was fucking me relentlessly and I was terrified of what Sarah wanted to do with her strapon.
“Oh fuck, I’m going to cum in your sissy boyfriend.”
I started to slam my hips back against him. Here in my lingerie and sexy dress, I wanted nothing more in the world than to make Mark cum inside me.
“Stop! Pull out of him, please Mark.” Sarah sounded worried, she clearly had something planned Mark could ruin if he got carried away.
Slowly, he drew his cock out of me and I stroked myself desperately as the feeling left me. Once out, he shoved me hard away from him and towards Sarah.
“I want you to cum on him!” Sarah said, pulling me up so I was kneeling in front of her, facing away.
Mark was directly in front of me and I and knew what was expected of me. I lifted up and slid back until I felt Sarah’s hand on my ass and her strapon pressing against me. Staring into Mark’s eyes, I sunk down and took her dildo all the way inside me. Mark pulled off his condom, came forward and shoved his cock into my mouth hard.
I bounced on Sarah’s dildo, losing myself in the feeling and enjoying her hands on my nipples and cock. All the while, Mark held my head and fucked my mouth. Opening my eyes, I caught sight of myself in the mirror. Sarah had pulled my dress down so my bra was exposed, leaving the dress bunched around my waist. My panties had come down around the top of my stockings, my cock stuck straight out as Sarah stroked it. I had never felt so sexy and so slutty, I pushed back hard against Sarah and eagerly waited for Mark’s cum.
I didn’t have to wait long. Mark pulled his cock out from between my lips and looked down at me smirking and stroking his cock. I reached down behind me and held Sarah’s thighs, riding her strapon hard and staring open mouthed at Mark. I was the picture of a wanton slut and I just wanted his cum. Watching me lose myself, he came. He moaned and his huge cock shot thick ropes of cum over my face and chest. I scooped it up and licked it off my fingers, never taking my eyes off Mark. I was still licking drops of his cum when my own hips started to rock uncontrollably, my cock shooting spurt after spurt into Sarah’s waiting hand.
Mark left the room quickly. Sarah and I disentangled, falling back onto the bed. She put her arms around me and held her hand to my lips. I could see my cum all over it and started to lick her clean.
“You did a really good job of fucking me, sweetie. More importantly, you made me so proud with Mark! You were such a little slut.”
I sighed and felt her pull my panties off. I straightened my dress, not really wanting to take it off and lay there whilst Sarah cuddled up behind me. I felt her strapon pushed between my cheeks and smiled.
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