Those Shoes Double Date

May 5, 2024 // By:analsex // No Comment

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** Getting Ready **

It takes me three days to fully recover from great sex, even if the love session ends in an ideal sex nap like it did with Rex and Jennifer. I put out so much energy on the bed, my mind and body are slow the next day. I felt lucky that we were not able to do a double date with Mike the next evening.

The plan was for a week from that night. That created its own problems. I would go to sleep at night. While you can tell how much I love to crossdress, I also love being naked. At night, I put on a pair of tight bikini briefs under my nylon shorts and nothing else. The problem happens at 5am. I feel really good.

And my 6 inch clitty feels really good and stiff. My shaved legs and torso feels really smooth on the sheets. And some little lizard brain program goes and has my fingers touch my shaved balls, and I mumble to myself, “Jennifer”, and now I have a throbbing hard-on. But its 5am, I know I should sleep more, but this rock hard boner starts from my pussy, travels along my taint, into the balls that are moving in the sack, all the way to the head. Such boners do not just “go away”.

I didn’t sleep well any night for a week.

Rex texted me the time to show up at his place to transform into Donna. I texted my wife about needing to go to the server farm two hours away. I told her it was just part of the six figure job. I still enjoyed her physically when she wanted to which was every other month. I would fuck her like crazy, thinking about my naked ass being entered as I fucked her. That was not going to happen. With Rex, there was no knowing what would happen other than it was going to be goo and intense and just all over the map. I love a love life that is complicated emotionally and physically. It was the lowest guys at the company that had to go to the server farms. The distant work did provide a way to have an intricate love life.

Rex gave me a key to his place. I enter and try to be super quiet. Rex does not want to see me as a man. It is not that he hates men, such the opposite. I know he has sex with men. How often, I don’t ask. And that is bull on bull macho sex. He said wants to see me as his gurl. He always calls me gurl. The label feels right since he is 7 inches taller than me, more than a hundred pounds heavier, wider than me. It was also not said with any form of disrespect which makes all the difference. I tiptoe to the bathroom to transform into his gurl.

Everything off. Oh I love being naked. Floor to ceiling mirrors so I can look at myself. I am 5′ 7″, 145 pounds, with a 29″ waist. I am a small size for a man. I never once saw that as an advantage – until I started putting on a soft blouse and skirt. Now I am a normal sized woman. Many gurls are normal sized men, or really big-boned women. Everybody’s body is different. I have really strong legs. One guy said while he was sliding into me side-by-side said he thought I had the legs of a hockey player. My legs are bulky and well defined, not sure why that is so. I am obsessed these days with my abs. I have horizontal lines which I love. I keep hoping to define the center one better. The line is there at the top, but fades out near the belly button. I call it my soft pack.

I am always noticing my cock. Part of my vision is always looking at my 6 inches. It is cut and medium thick. When it gets hard, it gets straight. I like to joke that proves I am not some sort of deviant homosexual, but those words get my straight cock to twitch and ooze some more precum. My clitty starts oozing precum at 5am when I know I will be visiting my stud. I am just like a girl except it is really obvious how much I am into sex with men. I am getting lost in looking and touching myself.

Oh, I almost forgot the best part: I keep her free of any hair. It is all so smooth and free and exposed. The bare balls look like they should be rubbed gently and licked. That would lead to licking the shaft. A mouth should take that cockhead in smoothly and glide down the shaft.

It takes me a little over an hour to get ready. Most of this part is not erotic. It feels technical, getting things right. The first thing is the full body shave. A gurlfriend recommended the Dollar Shave Club. I use their shave butter and 4x blades. I start with my clit area. She flies at half mast, enjoying both the feeling of being smooth and the attention. I take special care to make sure there was nothing around me tiny man nipples. They looks so clean and enjoy both soft wet touch and edgy pinches. A male lover of three years got me into the strong flavor of clean pits. Now mine are clean and smooth. No one at work has commented on my smooth arms, one good thing about being blond. My favorite part of bending over to shave my legs is the bending over. There is a lot of skin to work on, so I get to stay bent over a long time with my pussy up high and free.

Then comes Nair for Men. I swear it makes my ass feel just a little smoother. That one feeling alone makes it worth the bother. sex hikayeleri If you doubt me, I wish I could guide your hand up my skirt to feel one of my ass cheeks.

Full body moisturizing lotion comes next. This one product has changed how soft I feel everywhere. My skin is far from perfect, but now hands and legs and arms and torsos can glide over me.

I use LOTS of water and time, but no soap. I want my skin to taste of me. So many different tastes, the subtle ones of neck and nipple, the stronger ones of pits and balls and pussy. I can’t help but notice when a lover tastes all of me, even some toe sucking. We are then making full body love, a sensual, shared thing.

My citty remains at half mast. It takes a long time. I am aware of why I do it: to feel my erotic self. I do the same prep even if I am not going out on a date. This is me connecting with my body.

Time to towel off, another simple pleasure. I have to touch everywhere. I have to feel everywhere, what is still wet? Show self-affection, getting all areas dry. I catch myself in the mirror at work, naked, semi-erect, relaxed.

A little gurlie thing I to is to wrap the towel around me at nipple level as women do but men don’t. On the first night I used Rex’s key to slip in and take a shower, he came into the bathroom just as I was tucking in the towel around my chest. I felt this spark because I had just done this tiny feminine thing and here he was! He said he wanted me to think about something… I was curious and waited for him to say something. He didn’t. Instead his hand went under the towel, slid along my so smooth ass, and his middle finger found my pussy and slid in. I almost collapsed. He had put a dab of lube on that one digit so it felt like the most natural thing in the world. Up to the first knuckle and out. He had a playful grin and walked out. I was supposed to do makeup after that? I did think about what he did, and that evening… Sorry, different story but it was so good I keep taking risks for more pleasures like that.

This evening, at nearly the same time, he walked in, me clean in my femme towel wrap.

“I got something for you to wear.” He had a goofy grin on.

Rex let me make all fashion decisions. Something he held behind his back was fishy. It was a butt plug. It was a translucent purple with a narrow base, two round bulges, and a conical tip.

“I got one for Jennifer too.”

And then he went back to the kitchen beaming to listened to sports radio.

I had to lean against the vanity to not fall over. I know what a butt plug worn for a period of time does to my mind. I know I think about sex a lot. I am proud of that. The plug feels like a man is IN me now. I get desperate for any man. I look through Craigslist, think about going to the one book store that has booths for sex, or maybe driving two hours to a gay bath house. And Jennifer…

I have to focus on getting dressed. I walked into the bedroom to the lube drawer. Quick as a wink, I gave myself a shot of lube in my pussy. Clinical sex nurse at work. The purple butt plug got covered in lube and pressed into place.

I confidently strode back to the bathroom, dropped the towel, and put on my breast forms with the big nipples. On goes the lacy black bra. A simple outfit so far: bra and butt plug. If Rex had walked in then, I would have sucked his cock and demanded to be fucked on the vanity. If any man walked in, same deal.

Tonight it was fishnets. I get to bend over with a butt plug and put these black fishnet stockings on my oh-so-smooth legs. Bra, fishnet stockings, and butt plug, all works together says the full length mirror. And I should confess that without any touching, my clitty was three quarters full. On to the fishnet dress. Keeping the visuals going, I had some fishnet gloves. Then I have to figure out how much I have to cover up to be modest in public. I put on a white blouse with puffy shoulders that did not cover my midriff. My black leather skirt completed the outfit. I think it is too long, but most women would say the opposite.

I know I am kind of new to this, but I realized that I had forgotten to put on any panties. The butt plug worked its decadent magic in my lizard brain. What was the worst thing that could happen? Some guy notices there are no panties under my skirt. And he notices my now fully hard citty. He calls me a fucking sissy faggot. In a surprise move, I push him hard against the wall with one hand, the other hand goes to fondle is cock, and I say in my tough bitch voice, “Yeah, I am a proud fucking sissy fagot who needs your cum.” I go down on him and he cums quickly into my mouth. I smile at him with his cum giving my lips a special shine. As I walk away, lift up my skirt so he can see the plug. No panties needed tonight.

Now to slip into my black patent leather Merumote platform shoes! They are so simple and shiny. I love them so much, they will stay on throughout the evening no matter what happens. I picture porno hikayeleri myself on my back, Rex doing his sexy man work, and my Merumotes floating up to the ceiling. Bliss.

My wig is blond with big curls. Love long curls. Bright red lipstick of course. I caught myself thinking of the lipstick like a cock, but it is too small to do anything naughty with. I am too new to do anything fancy with mascara. I guess I still need a gurlfriend to help me out with that.

I told you, it does take a long time to transform. I looked at the results in the mirror. What was the overall look? Before I could answer the question, I felt the answer in my clitty. She was throbbing. I have been a man most of my life, loved and lusted for women who nearly always didn’t even bother to say no. Here in the mirror was a woman of my own dreams. She was strong which is a great thing when the sex gets all animal. Those smooth legs, magic to fondle because they lead up to a twink bubble butt. I lifted my skirt to flash myself.

And I wondered, how would my male self respond to that visual, a fully engorged phallus that was not a real pussy. I felt unsure. I flashed myself again. And I saw the answer in a glint of precum on my clitty. My male self would have said this is not what I expected. Yet sex is how we explore the most distant parts of ourselves. Time to enjoy lust with this gurl who can be both nice and nasty…

“You look hot gurl!” Rex started me, This time I felt a rush to my heart instead of my loins: He liked the look too. He deftly grabbed a glute under my skirt and gave it a squeeze. A quick kiss. “Gotta go, promised Mike we would be there at 9.”

I felt this pang because I wanted to give him a “let’s-stay-home-and-fuck-now” kiss, but he was a man with a plan, walking down the hallway to the car.

** To Club Jennifer **

Glad I was not behind the wheel. I had no ability to focus. Rex was driving his black Lexus in his black leather jacket. He is sooo big, filling up all the driver’s side with a huge torso. It doesn’t help me that he shaves his head clean and smooth and that reminds me of his cockhead. I wanted to give him a blow job while he drove to the club. I love cocks in all their various stages and forms. I was dreaming this would be that wonderful wake up phase when a cock is small and soft but smells so sharply of cock in makes me dizzy. He slips into my mouth easily, so relaxed. You feel the cock start to realize he has a warm, wet friend, but I don’t want to rush this phase. Every twitch and little growth throb makes me twitch and throb. Our lust grows together… no, Rex is driving and I am just thinking of sucking him off. Arg.

They have valet parking. What if I let Rex get out and let the young valet get in. He wore a red uniform that fit snug. I would tell the valet that my boyfriend was very strict and odd in his own way. He would not let me go into a gay night club unless I already had cum in my mouth. As I rubbed his thigh, I’d tell him I really want to do whatever is needed to go into this club…no more words would need to be said.

But that didn’t happen. I got out, the valet did have nice, tight red pants on. I wondered how often he was blown on a shift, if the sex made up for what was probably low wages. Maybe I would have given him more than the blow job, pulling out the butt plug so he could slide right in. I am going to trip on these 4 inch heels if I don’t stop thinking of having sex in public all the time.

The greeter’s at the door were young and good looking. They were both dark skinned and I would look so good sandwiched between them both. But they were professionals and took Rex’s coat. The club was loud and dark. It was both too much and too little. If I couldn’t blow the valet or do a three-way with the greeters, and Rex was, I don’t know where. I just felt lonely. Rex was at the bar, getting drinks as men always do. They do that so they can have their way with the ladies. Well, due to this butt plug, I wanted to go home and FUCK, no drink needed. Maybe I wasn’t feeling lonely, just horny and frustrated and a little angry. Whatever, not a good place.

Rex had the drinks and nodded to a table. I start strutting because I am in these high heels and then I stop.

Jennifer is at the table! I squealed and ran as best as I could. She jumped up from the table and made her best effort to run to me. OMG, she was in a red dress with a big skirt down about mid thigh. We hugged and squealed and giggled as our breasts smooshed together. She was bigger than me in every direction, even her clitty was bigger, but I didn’t care as I could feel it rub against mine. She gave me that first little playful kiss, but I swear she put just the smallest little bit of tongue in it, a way of saying to no one but me, yes, we had hot sex before, and will have more soon.

Mike was also at the table. He has curly jet black hair and big shoulders, a barrel chest, arms like trees. He wore a shirt that seks hikayeleri was unbuttoned so you could see his forest of chest hair. That forest of chest hair leads down to his black jeans that try and hide a thick cock and huge balls. I know, the cock and balls are the most masculine thing about a man, but his were so big and hairy, they just looked more manly than any other I had seen.

Rex handed a beer to Mike. “Did you give Jennifer a matching plug?”

I looked into Jennifer’s eye’s, she back into mine. More squealing and giggling. This I had to know. So my hand grabbed her ass, and she did the same. I really had to know and was too horny to care. I got my hand up her skirt and went for her butt crack. It was there! She was wearing some kind of satin thong and a butt plug. Jennifer apparently was making the same discovery, but she was pushing mine in! Oh fuck… We were kissing again, but sooo much deeper with our shared discovery. I pulled her plug out a little to tease her. It is remarkable we didn’t fall over. If we did, we might have had sex on the floor. I was dimly aware that Rex and Mike were enjoying our semi-public ass play.

“Who wants to dance?” Jennifer asked.

“We have beer to drink,” said Mike.

“Me, pick me!” I raised my hand.

She did grab my hand and tugged me toward the dance floor, but I resisted. I stood in her personal space, smelling her perfume.

“We need to dress fair”, I said, which clarified nothing for her until I deftly reached under her skirt and pulled her satin thong off. She step out of them quickly. “These are mine” and tied them to my ankle, adding a nice dash of color to my outfit.

“You are an evil girl, in a good way!”

Now we rushed off to the dance floor. Oh, I was so happy running away with Jennifer to the dance floor! Just jump and strut and bounce. It was the only time since Rex had plugged me that I wasn’t feeling pressure to suck cock or get fucked. She looked so hot and fun bounding around in that red dress without any panties on.

We were getting a good workout. She was so sexy bouncing in that red dress, her skirt flying up different amounts each time. As the strobes flashed, I had flashes of our tantric sex the last time together. Or the way she had fucked Rex. Or the way Rex had then fuck me. Or better than all that, our cum kiss and cuddle for our wind-down together. Did she remember all of that? Did all that matter to her like it mattered to me? I wondered how she felt about me.

And then she turn around, showing me her ass. That told me everything I hoped to know: she trusted me, she wanted me, and oh my God, her ass looked so sexy and inviting, knowing there were no panties under that skirt, knowing there were no panties under my skirt. There was never the thought of actually fucking in public, there was no need for that. She wanted me, I wanted her, and we danced to that hot vibe. Her ass was the perfect size, just big enough in a good way. I led her to turn around so I could present my ass to her. My ass is firm and tiny, smaller than any other girl out there. I couldn’t see her, but knew she must have been thinking the same things I was. We kept dancing that way in a cycle: face-to-face, me spooning her, she spooning me. One time where she turned to face me, arms up, we kissed. The dance floor with so much bouncing, and lights, and noise is not a great place to make out, but we needed to kiss, hands gripping hips to push them closer, clitty grinding on clitty. Such dance lust, bounding to the thump, bouncing to the lights, bouncing to the smell of her body in that red dress. I certainly don’t know how long we were dancing like that. Then I noticed both Rex and Mike on the dance floor, standing, not dancing.

“Time for you crazy sex kittens to go home.”

He was right

** Double Date at Home **

The same valet got our car. His ass still looked mighty fine, so I gave him a $20 tip. We drove home. I was unable to unwind, unable to think of anything but Jennifer in that red dress. I could smell both her perfume and sweat from the dancing. We arrived home, their car right behind ours. I did my awkward wave, but this time I know we could get through all that.

Rex and I stopped at the door to the master bedroom. Mike and Jennifer came to the same spot, Jennifer and I forcing a smile, so much nervous energy in the air.

Rex pulled out two condoms from his pocket, and casually said “Fuck each other.”

My confidence crashed. Rex and Mike went to the kitchen to talk about basketball. I couldn’t move. My dried sweat made me feel cold. I was so embarrassed, I wanted to call Jennifer an Uber. That was stupid, stupid, her car was here.

Rex can be such an ass, in a bad way. No, we were not going to fuck each other. I needed to rebel against that ass. Jennifer was looking at her feet. I stroked her hair and looked into her eyes. She raised her gaze.

“You are a bright, beautiful girl, no woman. You are a bright and sexy woman. We must make love, You only get two deep strokes inside of me. I only get two deep strokes inside of you.”

This was no longer for Rex. This was ours: Jennifer in Donna, Donna in Jennifer. Rex and Mike might watch, but I didn’t care.

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