We had been married for four years when my wife took on a new job, she was going to be the manager of a new insurance brokerage in our town but had to spend a few weeks of orientation and training at head office 180 miles away before she took on the responsibility. She spent the weeknights with an old university friend and would come home each Friday evening. We had a lively sex life and she was no prude when it came to sex and we had a lively sex life with a bit of role play thrown in to liven things up further. We were both interested in the sub side and took turns dominating each other on play nights. I’d rather sheepishly bought her a strap-on for a present and she had been game but we hadn’t had much success with it. We often heated things up by talking about the nasty things we could do with others, swinging, lesbian, even gay fantasies were all part of the role play. My interest in crossdressing in my youth was tucked well away, we discussed it like everything else about our past but it hadn’t been part of my life since my first serious girlfriend came on the scene, almost ten years ago.
When my wife was gone all week, the evenings were pretty long and boring. I went to the pub occasionally and played the odd game of squash but most evenings were spent alone. I watched TV, did a bit of gardening and DIY and chores. I thought to get all the laundry done during the week and Monday evening, pulling together all the discarded dirty clothes in the bedroom brought back some pretty horny memories from the night before, the black lace panties with the gusset stained from my dirty minded wife’s hot wet pussy were soon being inhaled whilst I rubbed my rapidly hardening cock. Soon I was naked, slipping them up my legs, then caressing myself to a crashing orgasm. Over the few days this developed into more dressing up for more elaborate and lengthy teasing sessions. I’m not an overly big guy and my wife, although slim and trim and sporty, is not a great deal smaller, her clothes fit me pretty well. She has a wide range of clothes that show off her gorgeous curves and since she was away for work, most of her sexiest clothes, including all the lingerie I had bought her, were alone at home with me.
I became obsessed with dressing up. I bought myself a pair of high heel sandals which was the only part of her wardrobe that didn’t fit me. I was dressing up every night and even sleeping in her babydolls and nightdresses. I fantasized about incorporating some of this rediscovered love of dress up into our bedroom games but knew it would need some planning to do it right and dreaded the ridicule or disappointment I might invoke if I approached it wrongly. Monday, Tuesday and Wednesday nights were filled with long sessions involving lingerie and makeup, taking lots of photos of myself in a multitude of poses, dancing and stripping, using vibrators and dildos and lots of lube and alcohol and porn and acting the slut for my imaginary lovers whilst slowly teasing myself closer and closer to orgasm. Often it was 2 or 3am before I allowed myself release.
One Thursday I dressed up and posed a little but I was exhausted from so many late nights and I needed to give my tired body and aching dick the night off to recover for my wife’s return on Friday. That was itself a delicious torment, wearing these sexy outfits but not allowing myself release. I set my alarm for 6am knowing that I would need time for a thorough cleanup before leaving for work then I slipped under the covers in the little satin babydoll and panty set I had bought my wife for her 25th birthday. I was fast asleep when my wife unexpectedly slipped into bed and slipped her arm around me, my dull mind registered her there but it must have taken a minute or two to fully seep into my brain and for me to realise that this was real and what the implications were. I think my heart stopped and then started pounding like a gong.
“Surprise, surprise, baby!” She cooed playfully in my ear. Her hand was slowly stroking my stomach, edging lower. My heart was thumping and I was desperately trying to think of a way out of this mess. Perhaps she hadn’t registered the satin of the nightie yet.
“You’re home!” I responded dully, my mouth thick with sleep.
“I worked late to get a day off and come home and surprise my hubby, but I guess the surprise is on me…. What are you wearing?” She was still light hearted but my heart sank.
“Oh, shit, I’m so sorry!” I mumbled, trying to open my eyes and take in the full reality of this situation. Trying to come up with an excuse and realizing there is no accidental way to end up in your wife’s lingerie.
“You will be sorry if you’ve stretched out any of my good clothes and, Fuck, you would have been if I’d seen you the moment I saw size 9 fuck me shoes, I was about to murder both you and your new girlfriend! You nearly gave me a heart attack!” She was lifting up and away from me as she spoke, lifting the covers as she went, exposing me to her calculating gaze.
“Oh, babe, I don’t have a new girlfriend!” It was a pretty lame thing to say but it was at least a diversion from the shoes.
“So I see, but it looks like I do! You have a new hobby it seems!” She said, a mocking tone entering her voice. “Tell all! We always promised no secrets and this is a pretty fucking huge one.”
“Oh, god, do we have to do this now? It’s the middle of the night!” I whined.
“Fuck, yes, we have to do this now! I had three cups of coffee to keep me awake on the way home then arrived to find another woman’s clothes around the house. Then I spent the last fifteen minutes discovering that, as far as I can see, your evenings alone have not been as boring as you make them out to be. I’m as wide awake as I’ve ever been, so talk!”
So I took a deep breath and told all, sitting in the semi-darkness with the streetlights lending a weird glow to the scene. I took pains to make sure that she was totally aware that I was doing this alone, no-one else was involved. She had a big tumbler of vodka and orange that she was steadily working at and she took a joint out of our bedside table, and it all seemed to calm her worried mind. She took it well, far better than I could have hoped or deserved.
I tried to surreptitiously remove some of the evidence: The ribbon holding my longish hair back in a ponytail, the big hoop clip on earrings, the lacy cuffs. But she stayed my hands, saying: “Don’t change a thing, I need to take this all in.” It was useless anyway, the evidence was everywhere, all over the house.
She quizzed me and mocked me a bit, but then she said: “Well, sweetie pie, it is fun wearing sexy clothes, and there is something sexy about you in this nightie and stockings, lying there all vulnerable and scared.” She started running her hand over me, caressing me. “You know it’s been years since I made out with a girl, there’s something soft and different about girlie sex, this could be fun!” She continued to run her hand over me, looking down at me with her drink in her other hand. “How long did you say you tease yourself?”
“All evening.”
“Mmmmm, so that could be hours! How long last night?”
“About three hours.” I answered
“Wow! You like that don’t you! You’ve always liked being teased!”
“Yes, or at least I like that feeling of being close to the edge.” I mumbled, embarrassed.
“What about Monday and Tuesday?”
“About the same, maybe even longer on Monday.”
She laughed: “Fuck! And how many times did you cum in that extravaganza?” She was playing with my cock now, running her fingers lightly along it, and it was responding to the feel of her fingers gentle caress through the thin sheen of nylon.
“Three.”
“Ahhhh! Good ones?”
“Yeah, because of the slow build up.”
“Better than the ones I give you?”
“God, no!” I exclaimed “But different.”
“Good answer!” She giggled. “So how many times did you cum this week?”
I had to think about it. “Six.” Damn it sounded a lot when I had to say it out loud!
“Huh! So whilst I have been a good girl and kept my hands out of my pussy all week for you, you have been pleasuring yourself quite indiscriminately! Wouldn’t you say?” She was beginning to slur her words, the vodka and weed taking effect.
“Yes.” I agreed a little cautiously, worried where this might lead.
“Yes.” She mimicked. “How about “I’m sorry, darling!” or “Please forgive me, dear!” or perhaps “I owe you six orgasms, M’Lady!” Remember the deal we had when I started commuting? That we would spend all week celibate so that our weekends would be full of the best sex ever?
“Yes, I’m sorry, darling.” I agreed sheepishly.
“And?” She grinned at me as her finger lightly flicked the head of my cock.
“I owe you six orgasms!” I conceded.
She just looked at me, eyebrows raised, her finger resting on my pulsing cock head, waiting.
“M’Lady!”
“Mmmmmmm, I like that! Six orgasms and you being subservient until I get them, then I may grant you your own orgasm. And then we can negotiate terms for the future. But until then, I own you, my little pet!” She had an evil grin on her face. “Not to say you won’t get a little pleasure out of it yourself, it’s always fun to tease! And you like a little pain too, perhaps more than I’ve felt comfortable with giving in the past . But now, in this role, I think we might be starting on a new adventure! I think I could enjoy mistreating a little girl slut! My own sexy little whore! What do you think? Are you up for it?” She flicked the end of my now rock hard cock.
“Yeah! You bet!” I agreed with a bigger grin than I meant to, relief and delight flooding through me.
“Fuck, you are such a perv!” She groaned, exasperatedly. “But that’s part of your attraction, I suppose, that and your big pay cheque and the way you take care of me, and understand me and your sense of humour and that you’re my best friend and….”
“My big dick!” I cut in, trying to bring her back to the point in hand!
“Ha!! Yes, Your big dick! Although until I get my big six, I think we might have to consider it a big clit, girls don’t have dicks!” She flicked the end of it. “Shame though, a sexy girl with big tits and a big dick could be the perfect bed toy!” She grabbed my flat chest, squeezing my nipples between her fingers and thumbs.
“You have little tits, whore! One more reason to make you suffer!” She pinched my nipples hard and I gave a little involuntary squeal of pain. She grinned again. “This is going to be a long night for you, whore! I’m wide awake, horny and feeling very vindictive! You ready?”
“Yes!” Damn right I was ready, I loved this woman and the way she loved to play.
She slapped my face, hard. “Address me correctly, slut, or you will feel nothing but pain!”
Fuck, that hurt, stung badly, she hadn’t held back. “Yes, M’Lady!” I corrected, shock clear in my voice.
“Better!” She grinned evilly again. “And that frightened look in your eyes is quite a turn on, we’ll have to encourage that!”
She ran her hand soothingly through my hair, then took a good grip and pulled me up and off the bed. I had no choice but to follow still dressed in the Linda’s sexy nightie. My body all too aware of the flimsy satin feel of it as the cooler air hit my skin.
“That’s such a slutty look for you, on your knees in hot pink satin and the black thigh highs with matching bows!” She walked around me, trailed her fingers over my panty clad bottom then gave it a hard slap. “Oh you have such a sexy bubble butt!”
“It’s all yours, M’lady.” I said quietly, trying not to sqeal from the slap. “I’m here to please you.”
“Undress me, you little slut! You have been pleasuring yourself all week, now it’s my turn. You are here to worship my body and to give me every satisfaction I crave. There is nothing else for you, you are here for my amusement. I hope your tongue is feeling strong because you are going to be lapping at my clit for a long time!” I reached up and started unbuttoning her blouse from where I knelt in front of her, thrilling at my new place in this turn of events, kissing every newly exposed piece of flesh.
“Good girl!” She said, relaxing her grip in my hair and soothingly stroking it down as I continued to undress her, shrugging off her blouse. “Now take my bra off, then I’ll let you worship my tits.”
I unhooked her bra and slipped the straps down so she could let it fall. I moved my face to kiss and suckle her gorgeous perky c cup breasts. She grabbed my hair and held me away from her. “Eager little bitch aren’t you! What do you say? How does a little subbie slut ask her mistress for a treat?”
“Please, M’Lady, may I kiss your breasts?” I simpered, falling readily into the part.
“Good girl!” She said, releasing me to worship her soft smooth flesh. “You like them, don’t you! Do you wish you had tits like mine? Big and soft and girlie. They would complete you, wouldn’t they! A big pair of sensitive tits for you to play with on your long lonely nights. You would like that wouldn’t you?
“Yes, M’Lady.” I confessed.
“You would look good with tits,” She said, her eyes closing as my lips enclosed a nipple, my tongue lapping at the sensitive underside. She groaned as my fingers found the other, rolling it gently between finger and thumb. “Ohhh, fuck! You are a good whore, don’t stop! Don’t fucking stop.”
She had sensitive nipples, and a couple of times when she had been really horny she had actually cum with nipple play alone and I reveled in the moans she was making as I toyed with them in my fingers and mouth. Greedily I feasted on her hard little pinched nipples, sucking and gently nipping at them with my lips and teeth, trying not to be too rough.
“Oh, fuck!” She gasped. “Oh, yesss! Like that, harder, harder! Make me cum!”
I continued nipping and pinching her nipples, rolling them between tightly pinched fingers. Snagging the nipples and the gorgeous soft undersides of her tits between my teeth and nipping hard, thrilled to be at the centre of her wanton lust. She ran her hands over my head and shoulders, playing with the straps and soft fabric of the nightie. Her climax built fast and hard, she arched her back and dug her nails into my shoulders as she squealed in delighted orgasm. I continued my fevered attack on her nipples, riding her over the crest of her wave, pinching, nipping, biting, her body bucking below me. Then more gently as her peak subsided.
She pushed me down off her now overly sensitive nipples, but she wasn’t done. “My pussy, eat my pussy!” She ordered, then laughed: “Fuck, I’m so fucking horny, I can’t wait to feel your tongue on my clit!”
I unclipped her skirt and slipped it and her panties down her legs. She lifted her hips to help me then rested back onto the pillows, pulling an extra one under her shoulders to prop herself up and improve her view. I lowered my face to her stomach kissing my way down, she started to part her legs for me and I could smell her warm scent rising to me, but then she closed them tight. I looked at her in surprise. “Ask nicely!” She demanded playfully. “I know that you know how!”
“Please, M’Lady.” I simpered. “Please may I taste your perfect pussy?”
“Oh, you shameless little slut!” She mocked. “You love eating my pussy, don’t you!”
“Yes, M’Lady.”
“I own you, sissy! Remember that as you eat me! I’m going to have fun with you, Sissy, I’m going to make you suffer!”
“Yes, M’Lady!” I said, a little worried.
“Mmmmmm, yesss, I’m beginning to like that scared little sissy look!” She slipped her legs apart and I bent to the task.
She slapped me, hard, across the cheek. “Not like that!” She hissed. “Get between my legs. Kneel, with your ass in the air and your face where it belongs! I want to see those panties while you eat me!”
Eagerly I moved and lowered my face into her gorgeous crotch, nothing but a little V of freshly trimmed pubic hair, her lips smooth and naked to my lips and tongue. I ran my tongue up and down the puffy lips, savouring the taste of her between them, delving and slurping at her moist pussy. She moaned her appreciation and I dug deeper, my tongue slipping between her folds and finding, first, her hot open pussy, soaking wet and eager to receive my tongue and then her hard pulsing clit. Her moans of pleasure as my tongue circled and delved into her pussy became louder and more frantic the longer and deeper I lapped into her and turned into gasps and then cries as I found and teased her clit with my tongue, lapping at it and flicking it in an insistent push towards her orgasm. I was rock hard in my panties as I greedily ministered to her in my favourite way. I watched her face, her pleasure evident in the sultry lust laden eyes, her mouth a perfect curve of joy. I worked with my tongue and lips, trying to read her every moan and movement to maximize her sensations.
She reached down and pulled my hands up to her breasts and my fingers had barely begun pinching her nipples when her hips bucked up into my face and she cried out in orgasm. I rolled her nipples gently between fingers and thumbs as my tongue continued to flick at her clit and another jolt hit her, then another. I focused in on her reactions and made my flickering tongue a little lighter and was rewarded with more and more jolts, her body thrashing and gasping under me, her hands in my hair, holding me tightly to her crotch. No sooner had one orgasm rippled through her then another came and took her again and again. She was greedily, wantonly abandoned in the sea of mindless bliss that was coursing through her and I couldn’t move my eyes, they were riveted to her face.
When a final wave took her she gasped loud in abandoned delight and pushed my face away from her panting and gasping for breath. I stayed there, kissing her thighs, her mons, her belly, feeling pleased with the orgasm I had given her, but still very horny and still wanting to give her more.
Slowly her breathing eased and she laughed: “Damn, you are good at that. You always have been, but that was one of the best!” She looked down at me. “Feel pretty pleased with yourself, don’t you!?”
“Uh huh!” I mumbled, grinning.
“Well, you have every right to! But that’s no way to address the woman that owns your pretty little ass!”
“Sorry, M’Lady!” I said in mock apology.
“You will be, when I’m done with your pretty little ass!” She said with a pointed look. She was enjoying this dominant role more than she ever had done before and I was loving submitting to her. She played with my hair as she looked at me and talked. “I like the pretty ribbon in your hair. Very girlie! Are you wearing makeup! Fuck, you have been really going for it haven’t you!”
I felt awkward and sheepish and began to move to a less visible position but she pulled hard on my hair. “Don’t move, sissy! I want you right there where I can get a good look at you.” She lifted my face a little and studied me in the poor light from the window. “Not a bad job, for a beginner!”
She teased me a little more about the makeup and about my choice of clothes and at one point she adjusted her legs and her foot found my cock. “My, My! We are an excited little sissy aren’t we! She rubbed my cock with her foot. “You’re leaking a little! Between, this thing stretching them out and leaking in them, they’re going to be ruined by morning. Look at your sexy little ass though! Yum! Since you look so cute in them you can keep them but you’ll be buying me new panties to replace them! Look at your sexy ass up in the air like that!”
She guided my face back to her pussy and I kissed her lips and began softly licking the sweet soft flesh. “Mmmmmm, that’s right, just like that! Oh, Yeah! What a pretty picture you make with your little pony tail and your silky nightie and your stockings on and look at that perfect ass! You know what would complete the picture?”
I couldn’t answer with a face full of my favourite pussy but it turned out the question was rhetorical anyway.
The End
