Suburbia
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Halloween In Suburbia free porn video
"So, the Russells are having a Halloween party. Susan and I thought it would be fun if we all went with a couples themed costume. The Russells are sending the k**s to her folks's for the weekend, so it's grown-ups only."
"That sounds nice," I said, barely registering what my wife said.
"We came up with pimps and ho's. What do you think?"
That caught my interest. Susan was hot. I mean, my wife was wonderful, and beautiful, and I loved her, but Susan was hot. I always had a hard time not gawking at her whenever she and Stan came over.
Two days later, the topic came up again. "Susan and I thought up a twist on the costume."
"What costume? What?" I asked. I'd completely forgotten about it.
"For the Russells' party. Remember? You agreed to go? We're going as pimps and hookers?"
"Oh. Yeah. That." Other than the promise of seeing Susan and my wife in slut gear, I wasn't all that interested. Although, there were a couple of other neighbors I wouldn't mind seeing dressed as naughty nurses, or schoolgirls, or slutty Ken Bones. I tried to put the idea out of my mind. I was happily married. Mostly. We'd been together for almost 7 years with few problems. No k**s. And we weren't trying to have any. Especially not lately.
"Don't you want to know what the twist is?"
"Huh? Oh. Yeah. What's the twist? Please tell me it's not blackface, Jen, because that's just not cool."
"What? No! No. The twist is you and Stan are the hookers and Susan and I are the pimps!"
"Uhhhhhh. What?"
"You and Stan dress up as hookers, and Susan and I are your pimps. It'll be fun!"
"I don't know about that."
"I'll make it worth your while," she said in a voice that promised sex. That was something we hadn't had in a long time. At least two months.
Two nights later, Friday, she came home from work with several bags. "We should practice."
"Practice what?" I asked.
"Making you into something someone would pay to have sex with, silly."
"What exactly are we practicing?"
"Well, for one thing, you're going to have to learn how to walk in heels. And, we need to see what makeup is going to look like on your. And we have to make sure these clothes fit. Now, let's get into the shower," she started undressing as she walked toward the master bathroom.
I guessed this was the "make it worth my while" part, and followed along, undressing myself as I went.
She was only wearing her white cotton panties when I walked in. I hadn't seen her naked in a while. She still looked good. I started to get hard.
"Not yet, silly. That comes later," she winked. "You're too hairy for a hooker. Here," she handed me a plastic bottle. "Rub this all over your legs, and then I'll help you shave the... hard to reach places."
I was all in. It was only leg hair. And it came off pretty easily. She helped me shave the rest of my body: chest, arms, underarms, and my back. And when it came time to shave my pubes and my ass, she was very delicate; teasing me with caresses as she went.
I had a raging boner when we were done, and figured I'd be fucking her soon. I was wrong. She rebuffed my overture with a playful, "Not yet!"
Next came makeup. It kind of killed my hard on. It was tedious and she was meticulous. But after about half an hour, she stepped back, and declared the work a triumph. Still, she wouldn't let me see. "Not until we see the finished product."
Back in the bedroom, she pulled on a satin nightie, and laid out my clothes for the party. There was a red bra and panty set with a matching garter belt. There was a black waist cincher. Black fishnet stockings. A pleather miniskirt. And a pink wife-beater style t-shirt with the word "slut" airbrushed on it. There were also 4 inch high heels. She helped me get dressed. The toughest part was the heels. Walk? Hell, I could barely stand in them.
"That's why we're practicing, Foxy!" she said as she slapped my ass.
The look was capped off with a short, neon pink wig, and a couple of clip on earrings. And finally, I got to see.
I won't lie. It wasn't bad. I mean, if I saw me walking down the street, I wouldn't spend more than $20 for a blowjob, but not bad all the same.
Jen thought so too. She didn't give me $20, but she did give me a blow job. Eventually.
"Hey, baby. You working tonight?"
"No sweetie, I just got off," I answered. "I'm looking for a party so I get really get off, sugar."
"You into girls? Because I've always been curious," her words were getting me horny again.
"Girls are my specialty, darlin'."
She lay back on the bed, and spread her legs. At some point, she'd taken off her panties. Probably when I was admiring myself in the mirror. Her bush had been shaved down to a landing strip, and my mouth watered. "Show me." She'd never been a big fan of receiving oral before, so this was a treat for me. Shall we say "worth my while?"
I went to work, kissing and licking her until she came. And when she came, she came hard, squirting all over my face. That was something she hadn't done before. Interesting.
I crawled back up to her and she was all about kissing me. Another new thing. It was like she suddenly loved the taste of her own pussy on my lips.
I held her for a while in between kisses, to give her a chance to catch her breath. I was exercising the patience of Job here, because I had slipped my dick out of one of my panty's leg holes, and was ready to give it to her good.
"Your turn," she giggled, as she got something out of the nightstand, and made her way down the bed.
My shoes had long since fallen off, and she proceeded to unfasten my stockings and pull them off. She started kissing the insides of my legs; it felt incredible without the body hair. I couldn't wait for her mouth to find my dick.
Her lips first touched my balls. And again: hairless = more sensitive. I know that now. I heard a buzzing noise, and an electric tickling sensation rushed up my backbone.
"Wh-wha-what was that!?"
"My vibrator. Like it? Since we're just a couple of girls playing here, I thought you wouldn't mind?"
"I... I do like it," I was suddenly out of breath. "Do... do it again."
And she did, applying the vibrator to my nutsack: touching and releasing, touching and holding. Goddamn!
I hadn't felt anything yet. She slid it down to my taint. That was somewhere she'd never ever gone near. And I regreted not having paid attention to it myself. I had had no idea my taint was so sensitive. And in a good way.
But that was just the warm up. She stopped the buzzing wand and touched the rounded end to my sphincter. I froze up. This was something completely new. And more than a little weird. Especially for her.
I heard Jen whisper. "I want to penetrate you. Please. I'll be gentle."
Years of masculine conditioning and homophobic cultural messages screamed "NO!" But the sensations my wife was giving me, combined with the pent-up lust mouthed the word "Yesssssssss." I whimpered my consent.
She withdrew the vibrator, and I stared at the ceiling through my false eyelashes as I heard a small plastic sound.
Jen shifted her position on the bed to get comfy and I felt the rounded tip touch me again. Only this time, it was wet. She'd put a lubed condom on it.
The vibrator wasn't large. Tapered at the end with a circumference of a quarter at its thickest. "Relax," she said, hushed and gentle. "Relax and push," as she kissed my inner thigh. I pushed, which seemed counterintuitive, as she was pushing too.
But it slid in. She let it sit for a second, to let me catch my breath. And I realized it didn't hurt. In fact, it find kind of... pleasant. Until she pulled it back. And pleasant turned to good. And then she pushed it, and good continued.
I couldn't believe this. Flat on my back, I was dressed like a slut, my legs spread and my wife was gently fucking me with her vibrator. And I liked it. I doubted it was going to get me off, but it was kinda nice.
Then she turned it on.
I must have passed out. That's the only explanation. Because otherwise, aliens suddenly beamed me out of the bedroom, and flew me through a supernova to the Garden of Eden, where I tasted the nectar of the gods.
When the stars left me and my feet hit the ground again, Jen was still between my legs, but licking my thighs and my cock.
She crawled up to me and kissed me again. She tasted funny. Salty. She pulled back and smiled at me. "You came so much! I'd never seen you come so hard before!"
I tried to respond but couldn't find words. She did all the talking. "Did you like that?"
I nodded.
"Think we should play like this again?"
Another nod.
I fell asleep in her arms, still dressed like a caricature of a hooker.
Saturday night, she insisted I practice walking in the heels. It wasn't easy but I was starting to get the hang of it. She did my makeup again, and we played again: I went down on her, and she vibrated the hell out of my ass.
Sunday afternoon, we didn't play.
But Monday evening, after work, over dinner, she asked slyly, "Do you want to 'practice'?"
Hell, yeah. Only this time, as she made me up, she explained what she was doing and how everything was supposed to fit together. I also practiced in my heels. I was getting good at it. Then we went to bed. I licked her and she toyed my ass to perfection again.
Tuesday evening: the same thing, but she had me do some of my own makeup.
Wednesday evening, she came home with more bags. I had cum all over the skirt and t-shirt so much that they were basically ruined. So, she bought me a new dress. And a full corset. And a new wig. But she wouldn't let me see until the party, which was Friday night.
I did most of my makeup that evening, with a bit of help from her, and we did our routine. Only it didn't feel like a routine. It was fun.
This time, when she was kissing my inner thighs, she paused. "I got something else. But I don't know if you'll like it?"
"What is it?"
"A new toy. It's bigger. Is that okay?"
It was. It was fine. It was good. It was a lot bigger, in girth and length. And she went slowly, and she went deeper with it. This one didn't vibrate though. But it was long enough to hit my prostate, which was good enough for me. I came everywhere, again, and this time, instead of licking it up and kissing me, she scooped it up with her fingers and fed it to me before we kissed.
We had an unconventional sex life, to say the least. As I fell asleep that night, I wondered what our suburban neighbors would think.
Thursday night, Jen went out with Susan to get their costumes. I stayed home and practiced by myself. I mean, I did my own makeup and walked around the house in the heels, going up and down the stairs and whatnot.
Oh, and I stuck the dildo up my ass and stroked myself to yet another shooting orgasm. (Jen was standing in the doorway as I came back to earth. I was embarrassed getting caught like that, but she thought it was cute. Not cute enough to let me go down on her again, but she was okay with it.)
Finally, it was Friday. I didn't realize it until I was at work, but I was actually looking forward to the party. My makeup looked good, my walk was sexy. I was actually kind of eager to show off my costume.
When I got home, Jen announced there was a change of plans. "We're not doing pimps and hoe's. It was tacky. Susan and I looked at the pimp costumes and just kinda got grossed out."
"Uh, so what are we doing?"
"High class escorts, and businessmen."
"What?"
"Basically you and Stan are still dressing up, and Susan and I are wearing suits, and slicking our hair down. It's kind of the same thing as it was. Just not as icky."
"Oh. Okay. So, um, what am I wearing?"
Jen pulled out the dress she brought home Wednesday. It was a tube dress. Bright red, with a scoop neck and a hem just above the knees. She also showed me the wig: jet black, long curly hair.
I wished she had let me practice wearing the corset, because it was tight and difficult to breath in. It also changed my balance, so I had to adjust my walk. (Just after I mastered the heels, too!) But it also gave me a nice curve to my waistline.
She put on a man's suit she picked up at a thrift store, and a fedora, and once we were both ready, off we went down the block to pick up Stan and Susan and head to the Russells'.
I didn't recognize the woman who opened the door. She was wearing a dress exactly like mine, only white. I wondered if we had picked the wrong house, when Stan spoke. "Damn. You look hot."
Yup. The hot redhead at the door was Stan. Susan was just as unrecognizable. She'd cut her long hair short and was wearing a fake goatee. Her suit was blocky enough to hide her famous curves.
We walked to the party on the next block; Susan and Jen walking and talking ahead of us, as Stan and I traded notes about which was the worst: walking so far in heels, not breathing with the corset, or the cold October wind on our legs.
The Russells always threw the best parties, and invited only the cool, fun neighbors. No-one recognized us at first when we walked in, but when they did, everyone had a good laugh. There were creative costumes everywhere you looked, and it made me appreciate how creative our neighbors were.
After a few glasses of punch, I no longer minded my feet hurting, or the repeated grabs at my ass. It became a running gag to see who could grab my ass or Stan's ass and get away before getting swatted.
I was just noticing that I hadn't seen Jen in a while when another hand touched my posterior. Only this wasn't a slap or a grab. It was a slow caress from my lower back, down to the cheek. And it didn't let go. I turned to find Stan standing next to me. "Hiya sexy. Are you into girls?" he asked breathily.
I laughed and slid my arm around his waist. "Considering all the men here are taken. There's a first time for everything, now isn't there?" I teased back.
He leaned in and whispered in my ear, "Seriously, you do look hot as fuck tonight."
It would normally be an odd thing for one man to say to another. But, it was Halloween, we'd had a couple of drinks, and I was proud of my appearance. "Mmmmm, so do you," I whispered back, noticing the hint of perfume he was wearing.
Damn. That's what I'd forgotten. Perfume! But, oh well, it wasn't like the night was ruined, now was it?
Stan's hand was still on my ass, and my arm was still around his waist.
That's when I saw Jen and Susan coming down the stairs from the upstairs bathroom. Maybe it was my imagination but it almost looked like they were holding hands when I first saw them. Susan's fake goatee had come off at some point during the party.
Jen looked a little flush when she came over to us. "Susan's not feeling well, so I'm going to walk her home, okay? See you later, hon?" She kissed me on the cheek and the girls left.
I said goodbye and was instantly distracted as someone slapped both my and Stan's asses. The party erupted in a roar of laughter, someone refilled my glass and the party continued.
Stan and I stayed pretty close to each other for the rest of the night; he was almost flirty, especially the way he kept touching me when we talked. In fact, I was getting used to it, so when he suggested we head out, and we held hands walking down the sidewalk, I hardly noticed it.
We got to his front walk, and I was going to continue home, when he invited me in. "The girls may be here," he offered, even though the house was dark.
They weren't, but he insisted on pouring me a drink before I left. "Please, sit down with me. My feet are killing me." I had to admit, mine were hurting too.
He sat close to me on the couch, closer than Stan normally would sit to me, but I chalked it up to him still being in character from the party.
He put his hand under my chin, and said "C'mhere. Hold still." I assumed he was going to brush something off my face, but he didn't. He leaned in and kissed me softly. On the lips.
I was shocked. Shocked!
He pulled back, smiling, "You're very beautiful tonight."
Before I could answer, he leaned in for another kiss. Only this time, his tongue hit my lips.
With the scent of his perfume in my nostrils, and the taste of his lipstick on my lips, I was still stunned. He pulled just an inch away from my face, and then leaned in for another kiss, his tongue darting out to touch my lips again. And again. And again. And then my lips parted, and his tongue found mine.
I did what came naturally. I kissed back.
His hand moved from my chin to my neck. His other hand slid up the outside of my thigh to rest on my hip. My hands were stuck in my lap, holding my tumbler. I think I actually forgot I had hands for a moment.
His lips moved away from mine, and my head moved forward to chase them, but he was targeting elsewhere. He kissed the corner of my mouth, then my cheek, my jaw, and then down my neck. I shivered, and felt the shiver reach down to my tucked away dick. The shiver was nice; the surge of blood to my folded back cock, not so much.
I let out a gasp as his lips continued to nibble my neck, racing up to my ear, which he nuzzled, and then back down. I was getting incredibly turned on.
His hand that was on my hip moved back to the top of my thigh, just where the hem of my dress was. He had long red nails, and he drew a little circle on my leg with one.
He pulled back from kissing and took the tumbler of whiskey from me, setting it on the coffee table, (without a coaster!), before taking both my hands in his.
He looked long and hard at me, before standing up, and pulling me up with him. My hands naturally went to his waist. We kissed again, before wordlessly, he turned, and led me up the stairs to the master bedroom.
The lights in there were on a dimmer switch, and Stan put them on low. We made out next to the bed for a few minutes, we me getting more and more turned on. I presume he was too.
I knew I was going to go for it. I was going to go all the way with my wife's best friend's husband.
My wife! His wife! I stopped kissing and he saw the look of worry on my face. He guessed what I was thinking. "Don't worry about them. They're not going to disturb us tonight."
That's when it all dawned on me. Susan and Jen holding hands. The whole dressing up for "Halloween." The teaching me how to look and walk and act like a woman. The taking a dildo up my ass. I'd been had. Susan and Jen were lovers. Stan, presumably, was in on it. I had been groomed, trained for this moment.
And I wanted it. I liked my anal orgasms. I wanted him to fuck me.
I pushed him backward onto the bed, and knelt down, kissing his inner thighs. They too had a hint of perfume about them.
Hell, I realized, I didn't just want him to fuck me. I wanted to suck him too. And I went forth aggressively, spreading his legs apart and kissing his dick through the lacy panties he wore.
I pulled the panties aside and let him spring free, all seven inches. (I later measured. Oh, and spoiler alert: this wasn't the only time for us. Not by a long shot.)
I took the head of his cock hungrily into my mouth. It looked like a giant pink mushroom, and to be honest, kind of felt like one too. I liked it, I realized. I licked and sucked as much of it in my mouth as I could, only stopping when he triggered my gag reflex.
I crawled up on the bed over him, kissing him a few more times, before stopping. I was hungry for one more thing. "Lube?" I asked.
He pointed to the nightstand, where a big bottle stood. I squirted some into my hand and started massaging his hard cock, getting it good and slimey. I kicked off my heels, pulled down my pantyhose and panties to my knees and climbed back, (awkwardly), onto the bed. Stan was still on his back, his dress pushed up to his waist, his big dick standing straight up out of his panties.
I straddled him and took him inside me. Surprisingly easily, considering he was thicker than the vibrator and the dildo I'd been 'practicing' with.
He was big enough that I knew, had I taken him all the way in, he would have hit my prostate, and it would have all been over. He would have been covered in my cum. And I wasn't ready for that. I wanted this to last for a while.
And it did. About two minutes of bouncing on his cock and I shot my load. Just like before, there was a lot and it went everywhere. When my vision cleared, I saw there was a big wad on his face. With him still in me, I leaned down and licked it off, only to return it to him with a big, gooey French kiss.
The movement forward reminded me of two things: he was still inside me, and he was still hard.
It wouldn't be fair for me to come and not let him come. I rolled off and lay down on my back. "It's your turn. Cum inside me."
He didn't hesitate. Stan was on top of me and inside of me within seconds.
I held out a lot longer before I orgasmed again. Probably about an hour. At least, that's what it felt like. It was probably closer to 3 minutes. But I came. With much less cum this time. In fact, he didn't notice. He was going to town so intently, he never broke the pace. And then I came again, and this time, something different happened: I think my sphincter tightened up or something, because he froze, gave out a groan, and then came.
After he pulled out, we lay next to each other kissing and fondling. Eventually, we undressed each other, pulling the wigs, clip-on earrings (although his weren't clip on,) dresses and undies off each other.
EPILOGUE:
Susan and Jen had been sleeping together for about six months before this night. Stan had been a lifelong crossdresser. Susan was okay with it, and shared the tidbit with Jen, who revealed she had lesbian fantasies.
It wasn't long before Susan and Jen realized they were in love. And it was about that time that Stan and I also fell. We kept both houses, and just switched. It was a little weird, and it made some of the neighbors uncomfortable. Especially when Stan and I decided to transition and live full time as women. Not all the neighbors were weirded out. In fact, some of the husbands liked to come over to our place to "watch the game" every now and then. And some of the wives loved Jen and Susan's "Book Club Nights."
But those are different stories for a different time.
"That sounds nice," I said, barely registering what my wife said.
"We came up with pimps and ho's. What do you think?"
That caught my interest. Susan was hot. I mean, my wife was wonderful, and beautiful, and I loved her, but Susan was hot. I always had a hard time not gawking at her whenever she and Stan came over.
Two days later, the topic came up again. "Susan and I thought up a twist on the costume."
"What costume? What?" I asked. I'd completely forgotten about it.
"For the Russells' party. Remember? You agreed to go? We're going as pimps and hookers?"
"Oh. Yeah. That." Other than the promise of seeing Susan and my wife in slut gear, I wasn't all that interested. Although, there were a couple of other neighbors I wouldn't mind seeing dressed as naughty nurses, or schoolgirls, or slutty Ken Bones. I tried to put the idea out of my mind. I was happily married. Mostly. We'd been together for almost 7 years with few problems. No k**s. And we weren't trying to have any. Especially not lately.
"Don't you want to know what the twist is?"
"Huh? Oh. Yeah. What's the twist? Please tell me it's not blackface, Jen, because that's just not cool."
"What? No! No. The twist is you and Stan are the hookers and Susan and I are the pimps!"
"Uhhhhhh. What?"
"You and Stan dress up as hookers, and Susan and I are your pimps. It'll be fun!"
"I don't know about that."
"I'll make it worth your while," she said in a voice that promised sex. That was something we hadn't had in a long time. At least two months.
Two nights later, Friday, she came home from work with several bags. "We should practice."
"Practice what?" I asked.
"Making you into something someone would pay to have sex with, silly."
"What exactly are we practicing?"
"Well, for one thing, you're going to have to learn how to walk in heels. And, we need to see what makeup is going to look like on your. And we have to make sure these clothes fit. Now, let's get into the shower," she started undressing as she walked toward the master bathroom.
I guessed this was the "make it worth my while" part, and followed along, undressing myself as I went.
She was only wearing her white cotton panties when I walked in. I hadn't seen her naked in a while. She still looked good. I started to get hard.
"Not yet, silly. That comes later," she winked. "You're too hairy for a hooker. Here," she handed me a plastic bottle. "Rub this all over your legs, and then I'll help you shave the... hard to reach places."
I was all in. It was only leg hair. And it came off pretty easily. She helped me shave the rest of my body: chest, arms, underarms, and my back. And when it came time to shave my pubes and my ass, she was very delicate; teasing me with caresses as she went.
I had a raging boner when we were done, and figured I'd be fucking her soon. I was wrong. She rebuffed my overture with a playful, "Not yet!"
Next came makeup. It kind of killed my hard on. It was tedious and she was meticulous. But after about half an hour, she stepped back, and declared the work a triumph. Still, she wouldn't let me see. "Not until we see the finished product."
Back in the bedroom, she pulled on a satin nightie, and laid out my clothes for the party. There was a red bra and panty set with a matching garter belt. There was a black waist cincher. Black fishnet stockings. A pleather miniskirt. And a pink wife-beater style t-shirt with the word "slut" airbrushed on it. There were also 4 inch high heels. She helped me get dressed. The toughest part was the heels. Walk? Hell, I could barely stand in them.
"That's why we're practicing, Foxy!" she said as she slapped my ass.
The look was capped off with a short, neon pink wig, and a couple of clip on earrings. And finally, I got to see.
I won't lie. It wasn't bad. I mean, if I saw me walking down the street, I wouldn't spend more than $20 for a blowjob, but not bad all the same.
Jen thought so too. She didn't give me $20, but she did give me a blow job. Eventually.
"Hey, baby. You working tonight?"
"No sweetie, I just got off," I answered. "I'm looking for a party so I get really get off, sugar."
"You into girls? Because I've always been curious," her words were getting me horny again.
"Girls are my specialty, darlin'."
She lay back on the bed, and spread her legs. At some point, she'd taken off her panties. Probably when I was admiring myself in the mirror. Her bush had been shaved down to a landing strip, and my mouth watered. "Show me." She'd never been a big fan of receiving oral before, so this was a treat for me. Shall we say "worth my while?"
I went to work, kissing and licking her until she came. And when she came, she came hard, squirting all over my face. That was something she hadn't done before. Interesting.
I crawled back up to her and she was all about kissing me. Another new thing. It was like she suddenly loved the taste of her own pussy on my lips.
I held her for a while in between kisses, to give her a chance to catch her breath. I was exercising the patience of Job here, because I had slipped my dick out of one of my panty's leg holes, and was ready to give it to her good.
"Your turn," she giggled, as she got something out of the nightstand, and made her way down the bed.
My shoes had long since fallen off, and she proceeded to unfasten my stockings and pull them off. She started kissing the insides of my legs; it felt incredible without the body hair. I couldn't wait for her mouth to find my dick.
Her lips first touched my balls. And again: hairless = more sensitive. I know that now. I heard a buzzing noise, and an electric tickling sensation rushed up my backbone.
"Wh-wha-what was that!?"
"My vibrator. Like it? Since we're just a couple of girls playing here, I thought you wouldn't mind?"
"I... I do like it," I was suddenly out of breath. "Do... do it again."
And she did, applying the vibrator to my nutsack: touching and releasing, touching and holding. Goddamn!
I hadn't felt anything yet. She slid it down to my taint. That was somewhere she'd never ever gone near. And I regreted not having paid attention to it myself. I had had no idea my taint was so sensitive. And in a good way.
But that was just the warm up. She stopped the buzzing wand and touched the rounded end to my sphincter. I froze up. This was something completely new. And more than a little weird. Especially for her.
I heard Jen whisper. "I want to penetrate you. Please. I'll be gentle."
Years of masculine conditioning and homophobic cultural messages screamed "NO!" But the sensations my wife was giving me, combined with the pent-up lust mouthed the word "Yesssssssss." I whimpered my consent.
She withdrew the vibrator, and I stared at the ceiling through my false eyelashes as I heard a small plastic sound.
Jen shifted her position on the bed to get comfy and I felt the rounded tip touch me again. Only this time, it was wet. She'd put a lubed condom on it.
The vibrator wasn't large. Tapered at the end with a circumference of a quarter at its thickest. "Relax," she said, hushed and gentle. "Relax and push," as she kissed my inner thigh. I pushed, which seemed counterintuitive, as she was pushing too.
But it slid in. She let it sit for a second, to let me catch my breath. And I realized it didn't hurt. In fact, it find kind of... pleasant. Until she pulled it back. And pleasant turned to good. And then she pushed it, and good continued.
I couldn't believe this. Flat on my back, I was dressed like a slut, my legs spread and my wife was gently fucking me with her vibrator. And I liked it. I doubted it was going to get me off, but it was kinda nice.
Then she turned it on.
I must have passed out. That's the only explanation. Because otherwise, aliens suddenly beamed me out of the bedroom, and flew me through a supernova to the Garden of Eden, where I tasted the nectar of the gods.
When the stars left me and my feet hit the ground again, Jen was still between my legs, but licking my thighs and my cock.
She crawled up to me and kissed me again. She tasted funny. Salty. She pulled back and smiled at me. "You came so much! I'd never seen you come so hard before!"
I tried to respond but couldn't find words. She did all the talking. "Did you like that?"
I nodded.
"Think we should play like this again?"
Another nod.
I fell asleep in her arms, still dressed like a caricature of a hooker.
Saturday night, she insisted I practice walking in the heels. It wasn't easy but I was starting to get the hang of it. She did my makeup again, and we played again: I went down on her, and she vibrated the hell out of my ass.
Sunday afternoon, we didn't play.
But Monday evening, after work, over dinner, she asked slyly, "Do you want to 'practice'?"
Hell, yeah. Only this time, as she made me up, she explained what she was doing and how everything was supposed to fit together. I also practiced in my heels. I was getting good at it. Then we went to bed. I licked her and she toyed my ass to perfection again.
Tuesday evening: the same thing, but she had me do some of my own makeup.
Wednesday evening, she came home with more bags. I had cum all over the skirt and t-shirt so much that they were basically ruined. So, she bought me a new dress. And a full corset. And a new wig. But she wouldn't let me see until the party, which was Friday night.
I did most of my makeup that evening, with a bit of help from her, and we did our routine. Only it didn't feel like a routine. It was fun.
This time, when she was kissing my inner thighs, she paused. "I got something else. But I don't know if you'll like it?"
"What is it?"
"A new toy. It's bigger. Is that okay?"
It was. It was fine. It was good. It was a lot bigger, in girth and length. And she went slowly, and she went deeper with it. This one didn't vibrate though. But it was long enough to hit my prostate, which was good enough for me. I came everywhere, again, and this time, instead of licking it up and kissing me, she scooped it up with her fingers and fed it to me before we kissed.
We had an unconventional sex life, to say the least. As I fell asleep that night, I wondered what our suburban neighbors would think.
Thursday night, Jen went out with Susan to get their costumes. I stayed home and practiced by myself. I mean, I did my own makeup and walked around the house in the heels, going up and down the stairs and whatnot.
Oh, and I stuck the dildo up my ass and stroked myself to yet another shooting orgasm. (Jen was standing in the doorway as I came back to earth. I was embarrassed getting caught like that, but she thought it was cute. Not cute enough to let me go down on her again, but she was okay with it.)
Finally, it was Friday. I didn't realize it until I was at work, but I was actually looking forward to the party. My makeup looked good, my walk was sexy. I was actually kind of eager to show off my costume.
When I got home, Jen announced there was a change of plans. "We're not doing pimps and hoe's. It was tacky. Susan and I looked at the pimp costumes and just kinda got grossed out."
"Uh, so what are we doing?"
"High class escorts, and businessmen."
"What?"
"Basically you and Stan are still dressing up, and Susan and I are wearing suits, and slicking our hair down. It's kind of the same thing as it was. Just not as icky."
"Oh. Okay. So, um, what am I wearing?"
Jen pulled out the dress she brought home Wednesday. It was a tube dress. Bright red, with a scoop neck and a hem just above the knees. She also showed me the wig: jet black, long curly hair.
I wished she had let me practice wearing the corset, because it was tight and difficult to breath in. It also changed my balance, so I had to adjust my walk. (Just after I mastered the heels, too!) But it also gave me a nice curve to my waistline.
She put on a man's suit she picked up at a thrift store, and a fedora, and once we were both ready, off we went down the block to pick up Stan and Susan and head to the Russells'.
I didn't recognize the woman who opened the door. She was wearing a dress exactly like mine, only white. I wondered if we had picked the wrong house, when Stan spoke. "Damn. You look hot."
Yup. The hot redhead at the door was Stan. Susan was just as unrecognizable. She'd cut her long hair short and was wearing a fake goatee. Her suit was blocky enough to hide her famous curves.
We walked to the party on the next block; Susan and Jen walking and talking ahead of us, as Stan and I traded notes about which was the worst: walking so far in heels, not breathing with the corset, or the cold October wind on our legs.
The Russells always threw the best parties, and invited only the cool, fun neighbors. No-one recognized us at first when we walked in, but when they did, everyone had a good laugh. There were creative costumes everywhere you looked, and it made me appreciate how creative our neighbors were.
After a few glasses of punch, I no longer minded my feet hurting, or the repeated grabs at my ass. It became a running gag to see who could grab my ass or Stan's ass and get away before getting swatted.
I was just noticing that I hadn't seen Jen in a while when another hand touched my posterior. Only this wasn't a slap or a grab. It was a slow caress from my lower back, down to the cheek. And it didn't let go. I turned to find Stan standing next to me. "Hiya sexy. Are you into girls?" he asked breathily.
I laughed and slid my arm around his waist. "Considering all the men here are taken. There's a first time for everything, now isn't there?" I teased back.
He leaned in and whispered in my ear, "Seriously, you do look hot as fuck tonight."
It would normally be an odd thing for one man to say to another. But, it was Halloween, we'd had a couple of drinks, and I was proud of my appearance. "Mmmmm, so do you," I whispered back, noticing the hint of perfume he was wearing.
Damn. That's what I'd forgotten. Perfume! But, oh well, it wasn't like the night was ruined, now was it?
Stan's hand was still on my ass, and my arm was still around his waist.
That's when I saw Jen and Susan coming down the stairs from the upstairs bathroom. Maybe it was my imagination but it almost looked like they were holding hands when I first saw them. Susan's fake goatee had come off at some point during the party.
Jen looked a little flush when she came over to us. "Susan's not feeling well, so I'm going to walk her home, okay? See you later, hon?" She kissed me on the cheek and the girls left.
I said goodbye and was instantly distracted as someone slapped both my and Stan's asses. The party erupted in a roar of laughter, someone refilled my glass and the party continued.
Stan and I stayed pretty close to each other for the rest of the night; he was almost flirty, especially the way he kept touching me when we talked. In fact, I was getting used to it, so when he suggested we head out, and we held hands walking down the sidewalk, I hardly noticed it.
We got to his front walk, and I was going to continue home, when he invited me in. "The girls may be here," he offered, even though the house was dark.
They weren't, but he insisted on pouring me a drink before I left. "Please, sit down with me. My feet are killing me." I had to admit, mine were hurting too.
He sat close to me on the couch, closer than Stan normally would sit to me, but I chalked it up to him still being in character from the party.
He put his hand under my chin, and said "C'mhere. Hold still." I assumed he was going to brush something off my face, but he didn't. He leaned in and kissed me softly. On the lips.
I was shocked. Shocked!
He pulled back, smiling, "You're very beautiful tonight."
Before I could answer, he leaned in for another kiss. Only this time, his tongue hit my lips.
With the scent of his perfume in my nostrils, and the taste of his lipstick on my lips, I was still stunned. He pulled just an inch away from my face, and then leaned in for another kiss, his tongue darting out to touch my lips again. And again. And again. And then my lips parted, and his tongue found mine.
I did what came naturally. I kissed back.
His hand moved from my chin to my neck. His other hand slid up the outside of my thigh to rest on my hip. My hands were stuck in my lap, holding my tumbler. I think I actually forgot I had hands for a moment.
His lips moved away from mine, and my head moved forward to chase them, but he was targeting elsewhere. He kissed the corner of my mouth, then my cheek, my jaw, and then down my neck. I shivered, and felt the shiver reach down to my tucked away dick. The shiver was nice; the surge of blood to my folded back cock, not so much.
I let out a gasp as his lips continued to nibble my neck, racing up to my ear, which he nuzzled, and then back down. I was getting incredibly turned on.
His hand that was on my hip moved back to the top of my thigh, just where the hem of my dress was. He had long red nails, and he drew a little circle on my leg with one.
He pulled back from kissing and took the tumbler of whiskey from me, setting it on the coffee table, (without a coaster!), before taking both my hands in his.
He looked long and hard at me, before standing up, and pulling me up with him. My hands naturally went to his waist. We kissed again, before wordlessly, he turned, and led me up the stairs to the master bedroom.
The lights in there were on a dimmer switch, and Stan put them on low. We made out next to the bed for a few minutes, we me getting more and more turned on. I presume he was too.
I knew I was going to go for it. I was going to go all the way with my wife's best friend's husband.
My wife! His wife! I stopped kissing and he saw the look of worry on my face. He guessed what I was thinking. "Don't worry about them. They're not going to disturb us tonight."
That's when it all dawned on me. Susan and Jen holding hands. The whole dressing up for "Halloween." The teaching me how to look and walk and act like a woman. The taking a dildo up my ass. I'd been had. Susan and Jen were lovers. Stan, presumably, was in on it. I had been groomed, trained for this moment.
And I wanted it. I liked my anal orgasms. I wanted him to fuck me.
I pushed him backward onto the bed, and knelt down, kissing his inner thighs. They too had a hint of perfume about them.
Hell, I realized, I didn't just want him to fuck me. I wanted to suck him too. And I went forth aggressively, spreading his legs apart and kissing his dick through the lacy panties he wore.
I pulled the panties aside and let him spring free, all seven inches. (I later measured. Oh, and spoiler alert: this wasn't the only time for us. Not by a long shot.)
I took the head of his cock hungrily into my mouth. It looked like a giant pink mushroom, and to be honest, kind of felt like one too. I liked it, I realized. I licked and sucked as much of it in my mouth as I could, only stopping when he triggered my gag reflex.
I crawled up on the bed over him, kissing him a few more times, before stopping. I was hungry for one more thing. "Lube?" I asked.
He pointed to the nightstand, where a big bottle stood. I squirted some into my hand and started massaging his hard cock, getting it good and slimey. I kicked off my heels, pulled down my pantyhose and panties to my knees and climbed back, (awkwardly), onto the bed. Stan was still on his back, his dress pushed up to his waist, his big dick standing straight up out of his panties.
I straddled him and took him inside me. Surprisingly easily, considering he was thicker than the vibrator and the dildo I'd been 'practicing' with.
He was big enough that I knew, had I taken him all the way in, he would have hit my prostate, and it would have all been over. He would have been covered in my cum. And I wasn't ready for that. I wanted this to last for a while.
And it did. About two minutes of bouncing on his cock and I shot my load. Just like before, there was a lot and it went everywhere. When my vision cleared, I saw there was a big wad on his face. With him still in me, I leaned down and licked it off, only to return it to him with a big, gooey French kiss.
The movement forward reminded me of two things: he was still inside me, and he was still hard.
It wouldn't be fair for me to come and not let him come. I rolled off and lay down on my back. "It's your turn. Cum inside me."
He didn't hesitate. Stan was on top of me and inside of me within seconds.
I held out a lot longer before I orgasmed again. Probably about an hour. At least, that's what it felt like. It was probably closer to 3 minutes. But I came. With much less cum this time. In fact, he didn't notice. He was going to town so intently, he never broke the pace. And then I came again, and this time, something different happened: I think my sphincter tightened up or something, because he froze, gave out a groan, and then came.
After he pulled out, we lay next to each other kissing and fondling. Eventually, we undressed each other, pulling the wigs, clip-on earrings (although his weren't clip on,) dresses and undies off each other.
EPILOGUE:
Susan and Jen had been sleeping together for about six months before this night. Stan had been a lifelong crossdresser. Susan was okay with it, and shared the tidbit with Jen, who revealed she had lesbian fantasies.
It wasn't long before Susan and Jen realized they were in love. And it was about that time that Stan and I also fell. We kept both houses, and just switched. It was a little weird, and it made some of the neighbors uncomfortable. Especially when Stan and I decided to transition and live full time as women. Not all the neighbors were weirded out. In fact, some of the husbands liked to come over to our place to "watch the game" every now and then. And some of the wives loved Jen and Susan's "Book Club Nights."
But those are different stories for a different time.
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