Briefs No. 03: My Wife’s Friends

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While sliding my silk stockings up my newly shaved legs, I thought about what got me here. My wife, Madison, told me after I’d been transformed that she’d planned this since before we married. She said she’d dated a boi in college for a while until the boi had been stolen from her by one of their professors. Said she’d liked the concept, if not the result. She said she’d known I had potential from our first date, and when I proposed, she’d made a detailed plan.

That was why, when I opened my suitcase on the first morning of our honeymoon, I found various styles of panties instead of my boxers. And instead of my swimming trunks, I’d found a couple of two-piece women’s suits. I was so in love and so oblivious that I’d bought Madison’s explanation that: “Customs was probably going through your case and someone else’s at the same time and got the undies mixed up. I mean, that explains the bra too.” Then: “And there’s no real difference between bikini bottoms and a Speedo.”

When we got home, she told me how much she liked seeing me in those panties and I reluctantly agreed to keep wearing them. I mean every time I agreed to do something like that for her, the sex was amazing for the next few days.

Somewhere along the way I realized what she was doing. I mean I did some research on the net and found out that feminization was a thing. I confronted Madison about it; asked her why she was turning me into a sissy. She looked at me with those big, gorgeous green eyes and said: “Because it’s sexy as fuck and it makes me happy. Doesn’t it make you happy?” I melted and said I it did and the next thing we were both in our sexiest lingerie fucking madly on the bed.

Things changed rapidly for a while. My Kindle filled up with stories about forced feminization and I kept getting emails pointing to sissy videos that “someone” (named Madison, of course) had sent me as a gift. Madison started calling me “Darlene” in private and in public when we were out and I was dressed. Yes, that’s when she started taking me out in public where no one we knew would be.

The hormone pills started arriving for me at the beginning of each month. And Madison put me on a diet and exercise regime designed for women. I was en femme every evening when I got home from work and all day every weekend. We even joined a Unitarian congregation so that I would have an excuse to get dressed up and out every Sunday. And we began to make friends that never even knew my male self existed.

But something more would change tonight, I thought, hooking my bra behind my back, capturing my tender, small-but-growing, breasts in silky cups. Tonight was our wedding anniversary and for the weekend we would be hosting Kendra, Madison’s roommate from Junior and Senior year in college along with Kendra’s husband Marcus. This would be the first time anyone from my past life had ever met Darlene.

Well, I thought again as I pulled my frilly black panties up over my stockings and garter and tucked my shrunken and shaved junk between my thighs, Madison would be hosting. Tonight I was just the maid and the rest of the weekend, I’d be whatever the three of them wanted me to be.

My uniform tonight was a black dress with white trim and short sleeves with puffy shoulders, two-inch black heels and a white cap. After I’d pulled that on, I made sure my make up was done and the jewelry that Madison had selected for me was in place. I was wearing hoop earrings and a silver cross on a silver chain around my neck. Around my left ankle was a silver charm anklet with a Venus sign, a representation of a vulva, a transsexual flag, a pair of boobs, and various other risqué charms Madison had found for me.

The doorbell rang. It was too early for Marcus and Kendra. “That’ll be the caterer, honey,” Madison called from the bathtub. “Be a dear and go get it. Tip them well!”

I made a face but remembered I was the maid tonight, so I went to answer the door to our apartment after grabbing my wallet from my purse. The woman waiting in the hall was hard bitten and covered with grease from deliveries. She carried an insulated bag in front of her. She looked me up and down, smirking. “Costume party?” she asked flatly.

“Um, not really,” I said. “The kitchen is this way.”

“Don’t tell me you’re a maid all the time.”

“We’re just having some old friends over.” I said as she put down the bag and pulled out four dishes, naming each. I signed her form and paid her, adding a nice tip.

“Cause if you do this for pay, I can get you some gigs.”

“No, that won’t be necessary.”

Madison walked into the kitchen then, a robe on, but not closed. Her face smiling; her breasts high and tight; her blonde bush full. “Did you pay her?” she asked me. I nodded.

The girl gave my wife an appraising look. “A sex party, then? I’ve got some E…” She whipped a little plastic bag from her pocket.

“That won’t be nec…” I started but Madison interrupted.

“That would be fun. Four please. Pay the woman, Darren.” I winced at her using my masculine name. The girl gave me a glance, çekmeköy escort reappraising.

“How much?” I asked.

She named a price. “But I’ll give you yours for free, baby, if you let me cop a feel,” she said to Madison, who giggled.


The woman stepped up to my wife and her hand went right between Madison’s legs. Madison moaned and the woman said, “Oh, you’re so wet.” I saw a range of emotions on my wife’s face and then she grabbed the woman’s wrist and moved the fingers out of her. “That’s more than copping a feel, girlfriend,” she said but didn’t seem mad.

“Yeah, well,” the woman sucked Madisons slipperiness of her fingers, then held them out to me for payment. She handed Madison a card. “If you ever need more E, or anything else, here’s my number. C’mon, Darren, show me out.”

She copped a feel of my ass before she left, whispering. “Seriously, I can make good money for you,” before I closed the door.

“That was unexpected,” my wife said, when I came back to the kitchen. She’d closed her robe.

“Very,” I said.

“But fun. I’m going to get dressed. You know what to do. Don’t forget both the dry and sweet vermouth.”

I looked at the clock. Half an hour to their arrival; I had plenty of time. I arranged the hors d’oeuvres on a couple of plates, got out our fancy napkins, made sure the white wine was chilled and the red was breathing, and arranged a number of glasses for wine or martinis.

Madison came out of the bedroom looking stunning. Her hair was artfully lifted on her head with a few strands hanging strategically downward. Her makeup was to die for. And she was wearing a very-short, red, sequined cocktail dress with spaghetti straps. It emphasized her boobs something wonderful. On her feet she was wearing red-3 inch fuck-me heels.

I was speechless for a minute, just reveling in her beauty. Once again I felt like I was the luckiest man alive. Or maybe the luckiest sissy? I was about to say something when the doorbell rang again.

“That’s them, darling. Go answer the door. And remember to curtsey.”

“Yes, ma’am,” I said, putting on my best maid face.

I took a deep breath before I opened the door, then I turned the handle and pulled it back. I ducked into a rather humiliating curtsey and said, “Hello, may I help you?”

“Darren? Is that you? Oh my God!” The woman addressing me was Kendra, of course. She was a well-proportioned black woman with straightened and blonde-dyed hair. Her breasts and hips were well-sculpted curves that seemed to have been designed by an ad agency. Her lips were painted cherry red and she was wearing a purple, above-the-knee party dress under her light coat. Her smile was only slightly less dazzling than Madison’s.

Just behind her was a six-foot-two-inch tall black man wearing an “untucked” shirt and tailored slacks. He was everything I’d never been, fit, muscled, and handsome. His pants bulged in the front in a very suggestive way. I was instantly jealous. Or … or something; it was confusing.

“Yes, ma’am,” I said. “But I prefer Darlene. Or you can just call me ‘maid’ tonight.”

“Maid? I like that,” she laughed. “Spin for me, maid!” I did as instructed. “Isn’t she adorbs, Marcus? Don’t you want to just bend her over the counter and fuck her?”

I blushed. Marcus said, “She is quite cute for a sissy.”

Kendra gave him a playful punch. “Loosen up, big guy. This is a fun weekend.”

“Is that you, Kendra?” my wife called from the living room.

She squeed and rushed past me, her arms in the air and obviously delighted to see Madison. That left me alone with Marcus. “Just how much of a sissy are you?”

“As much as Madison wants me to be, sir.”

“Hmm, we’ll see.” He stepped into the foyer and indicated the two bags that they’d brought. “See that these go to our bedroom then, honey.” On my way past, he patted me on my ass, once, then twice. My blush never cleared. Then he headed toward the living room.

I shuffled to hold the door open and pull in the two suitcases to bring to their room. When I got to the living room, Kendra and Madison were just breaking away from a kiss that had been anything but chaste. I mean I saw tongues slipping back into their mouths. Madison slipped into an equally passionate kiss with Marcus and I was once again jealous. Confusingly, I didn’t really know of whom.

I stashed the suitcases in the guest bedroom and came back to the living room. Madison saw me and said, “Who wants what to drink? Darlene makes a killer martini.” They all decided on those and I scurried into the kitchen to mix three and pour them into the proper glasses. I put those on a tray and brought them back.

In the living room again, I was treated to the sight of Madison and Kendra lip-locked again. It was so beautiful to see the two of them like that, their skins such a beautiful contrast. Madison had told me that they were sometime lovers in college and she missed having a girlfriend, so I wasn’t totally surprised. I also wasn’t surprised that with her cevizli escort dress creeping up her hips, I could see my wife was still not wearing any panties.

I handed out the Martinis and Madison said: “Go get the little silver tray, Darlene, darling.” It only took me a second and I came back with a tray with four little pills on it. “A little ecstasy for the night?” she asked with a quirky smile?

“I’ll take one,” Marcus said. Joined by a “Oh, hell, yah,” from Kendra. Madison took hers and the three of them chased them down with swigs from their glasses.

“Go make us three more drinks, darling,” Madison told me. “And go take your pill too.”

I thought about not taking it, but decided I wanted it, so I swallowed mine down with some water and then made new drinks.

When I got back, I wondered why they bothered with the E. It couldn’t have taken effect yet, but Madison was on her knees in front of Marcus. She had his large, coffee-colored member out and hard and she was just starting to take it in her mouth. That’s it, I thought, I’m officially a cuckold now.

But that wasn’t all that was going on. Kendra knelt behind my wife, pressed against her back. Kendra’s dark hands were squeezing Madison’s breasts from behind. It looked like she might be rubbing herself on Madisons foot as well.

Marcus noticed me come in — I personally wouldn’t have been able to take my eyes off the two women in front of me — and waved me over so he could take a drink. He smiled a shit-eating grin up at me as his cock disappeared entirely into my wife’s mouth. She pumped her head up and down on it a couple of times, making gagging sounds — mine wasn’t big enough for that to happen — before lifting her head and, drooling a little, smiling up at Marcus.

“Oh, I can’t wait for you to fuck me,” she breathed, heavily at him. Then I saw Kendra slide back and pull Madison’s dress up and over her head, leaving her naked. At the same time Marcus put his drink back on my tray and his cold hand trailed up the back of my leg and came to rest on my panty covered bottom. I shivered from everything happening.

Madison’s mouth came back to Marcus’s cock, her long, wispy blonde hair spreading over his dark lap like a napkin. She hungrily took him back into her mouth, moaning with delight. Marcus was moaning too.

Kendra took the moment to stand up, divest herself of her dress and come to me for her drink. She took the tray from my hands and put it on the table. Then with her martini in one hand she pulled me forward for a kiss as intimate as the one’s she’d given Madison, even as her husband’s hand started to push its way between my legs from behind. I shifted to let him, because the E was starting to take effect on me and because Madison had told me that I should let our guests do whatever they wanted to me.

His hand came flat on the front frills of my panties. “I thought you said she still had a dick,” he said to Kendra, clearly surprised. “I can’t feel one.”

Madison surfaced from the ocean of pleasure she was enjoying to look up and say, “Oh it’s there. Just safely tucked away for the moment.”

“Let me feel!” Kendra almost squealed. “Let me see.” Her hands were soon under my skirt but she pushed her fingers under the waistband of my panties. I shivered with pleasure as her fingers slid over my smooth “mound,” then down further. “Oh, I feel it,” she said. “Tucked between his legs. How do you stand that you poor thing?” she said before backing off from me.

She undid her bra, revealing her dark, natural, large breasts, with coffee-colored areolae and perky nipples. She grabbed my hand. “My husband’s gonna fuck your wife, like he’s wanted to do since your wedding day. And you’re gonna eat me out while I watch.”

She pulled me toward one of the easy chairs while Madison got up from the floor, after pushing Marcus’s pants all the way off. He was taking his shirt off as well. I saw Madison turn around and face away from Marcus, then slowly slide her obviously slippery, blonde covered pussy down Marcus’s long, thick, cock. Her eyes closed when his tip slipped between her lips and she smiled like a cat with cream. As she lowered herself further, her lips formed an oh and her eyes opened wide, sparkling. “Oh, God, Kendra, he feels so good.”

“All yours girlfriend,” Kendra said cheerfully. Then to me, “Now you get your sweet lips on my sweet lips. Don’t let those two have all the fun.” As I got down on my knees, hoping I wouldn’t put a run in my stockings, Kendra parted her legs. She was smooth shaven down there, with her clit sticking up prominently, and spreading out from the peak. As she opened wider, I could see the bright pink of her insides.

“Would you like it fast or slow?” I asked looking up at her.

“Aren’t you so adorable like that, Darlene. I want it fast at first. I’ll tell you to slow down.”

Madison was moving on Marcus’s cock and now moaning with the feeling he was bringing her. I went right for Kendra’s clit and was rewarded with her own moan in return. She smelled so different erenköy escort from Madison and so much the same. Kendra was more peppery, I think, but I could say more when I tasted her more fully.

I swirled my tongue around her pink clit, then surrounded it with my lips sucking and pistoning like Madison likes so much. “Oh, baby,” Kendra said to me at almost the same moment Madison let out an “Oh fuck me” from deep down in her throat. “Squeeze my tits,” I heard her say. “Harder, no harder. Oh fuck yes.”

I slid three fingers from my right hand into Kendra’s slippery warmth and began to pump them out and in as I flicked my tongue like a snake’s quickly back and forth on her clit.

“Madison, baby,” Kendra called. I looked up and she was playing with her own nipples, pulling them, twisting them. “Oh baby, you look so good fucking Marcus. So good. Ride him baby. Ride him hard. Oh, God!” she added and pushed her pussy hard against my face. I went back to sucking on her clit and turned my fingers up to her G-spot.

“Oh fuck, I’m cuming,” my wife screamed, her voice an octave higher than normal. “I’m cuming. I’m cuming. I’m ooooooooooh!” she cried.

“Oh, me too,” Kendra echoed. “Me fucking too. Fuuuck!” she called and I felt her pussy crush my fingers together and get even wetter and her breath came rapidly. She grabbed the front of my hair and pulled me away from her. I could see my lipstick smeared all over her and realized my makeup was a mess.

“I want you on top of me,” Madison growled and I heard her move off Marcus and then felt her shoulder against my feet as she laid down on the floor.

“Okay, now slower, lover,” Kendra said down at me. “While my husband fucks your wife with his beautiful black cock.” I imagined Madison spread herself for Marcus, hungry to be fucked by him.

Kendra pulled me back to her pussy and I pushed between her lips with my tongue, tasting her fully, smearing my face with her juices. She was, I decided, indeed more peppery than Madison. But every bit as delicious and I hungrily licked every inch of her that I could lick, only occasionally reaching up to her clit.

I felt Marcus’s arm or shoulder hit my feet and Madison reacting with a long sigh of delight. He must have slid into her. I found it surprisingly sexy touching him when he was fucking my wife. But he was only in contact with me for a moment before he lifted himself up and started pumping into Madison.

“So good, so good,” Kendra was repeating above me while Marcus grunted and pushed Madison against me and then away again. Madison was moaning or calling “fuck me, fuck me,” and her breath was coming quicker and quicker. I was amazed that Marcus could hold back so long while giving one – and soon two – orgasms to my wife.

Kendra started humming, her pitch slowly rising and Madison was softly saying, “Oh. Oh. Oh!” over and over again. They both seemed close. But Kendra got off first, her hum turning into a high pitched long lasting “Ah,” and her pussy pushing my tongue out from the deep place I’d gotten to. Madison’s arm suddenly slapped into my legs and her other hit the couch. “Oh fuck! Oh fuck! So fuckin’ good.”

“Did you cum?” she asked, breathlessly. “Did you cum? I want you to cum in me,” she panted at Marcus. “Cum in me. Fill me up you beautiful man. I want your cum in me. I want it all. Is this good? Is this good? You want me to turn over? You want my ass?”

“No baby. Just stay there.” But I could somehow tell that he’d lifted her legs above his shoulders and was pounding into her again.

Kendra moved. “I want your tongue in my ass,” she said to me. “Lick my black ass, bitch.” She shifted in the chair, rotating her hips and lifting her legs up high and I was looking at her asshole, pink and tight. This wasn’t something I’d ever done before and I hesitated for a moment, then I shrugged and bent forward.

I began by just licking up and down between her cheeks, getting used to the idea of what I was going to do; getting used to the taste. It wasn’t as bad as I had expected. It was earthy, spicy, and inciting. Marcus was pounding hard into Madison behind me, eliciting all manner of cries and whimpers from her. I was envious of her, surprisingly, imagining that huge, hard cock splitting me in two. But I didn’t have a pussy and I wasn’t gay.

I pushed my tongue into Kendra’s puckered hole, causing her to squirm and moan. “That’s it, sissy. That’s it. Deeper. Deeper,” she called to me. Her hole was so tight and it was hard, but I pushed in deeper like she demanded. Madison cried out from another orgasm behind me and Kendra reached between her legs and began rubbing her own clit like she was possessed by a demon. I pushed in and out of her asshole, fucking it as best I could. There was a strange tang on my tongue and it was starting to hurt, but Kendra was clearly enjoying it.

Behind me, I heard Marcus grunt and sigh and stop moving. “That’s it, baby, that’s it,” Madison was saying. “Oh, baby, pump it into me. Pump it all into me. Oh God, oh God!” She seemed to be cuming again. Kendra suddenly called out “Jesus!” Her whole body tensed up and my tongue felt like it was squeezed like an orange. I saw liquid actually squirt out from Kendra’s pussy. It fell on her stomach and her thighs and my face. She pushed me away from her cunt, panting.

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